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m-Phenylenediamine

PubChem CID
7935
Structure
m-Phenylenediamine_small.png
m-Phenylenediamine_3D_Structure.png
m-Phenylenediamine__Crystal_Structure.png
Molecular Formula
Synonyms
  • m-Phenylenediamine
  • 108-45-2
  • benzene-1,3-diamine
  • 1,3-Phenylenediamine
  • 1,3-BENZENEDIAMINE
Molecular Weight
108.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-04
Description
1,3-phenylenediamine appears as colorless or white colored needles that turn red or purple in air. Melting point 64-66 C. Density 1.14 g / cm3. Flash point 280 F. May irritate skin and eyes. Toxic by skin absorption, inhalation or ingestion. Used in aramid fiber manufacture, as a polymer additive, dye manufacturing, as a laboratory reagent, and in photography.
1,3-phenylenediamine is a phenylenediamine taht is benzene substituted at positions 1 and 3 with amino functions.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
m-Phenylenediamine.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzene-1,3-diamine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

WZCQRUWWHSTZEM-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC(=CC(=C1)N)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H8N2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C6H8N2

C6H4(NH2)2

2.3 Other Identifiers

2.3.1 CAS

108-45-2

2.3.3 Deprecated CAS

1266121-34-9, 1274866-89-5
1274866-89-5

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 UN Number

2.3.7 ChEBI ID

2.3.8 ChEMBL ID

2.3.9 DSSTox Substance ID

2.3.10 HMDB ID

2.3.11 ICSC Number

2.3.12 KEGG ID

2.3.13 Metabolomics Workbench ID

2.3.14 Nikkaji Number

2.3.15 NSC Number

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,3-diaminobenzene
  • 1,3-phenylenediamine
  • 3-phenylenediamine
  • m-phenylenediamine
  • meta-phenylenediamine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
108.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
108.068748264 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
108.068748264 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
52 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
64.9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

1,3-phenylenediamine appears as colorless or white colored needles that turn red or purple in air. Melting point 64-66 C. Density 1.14 g / cm3. Flash point 280 F. May irritate skin and eyes. Toxic by skin absorption, inhalation or ingestion. Used in aramid fiber manufacture, as a polymer additive, dye manufacturing, as a laboratory reagent, and in photography.
Pellets or Large Crystals, Liquid; Pellets or Large Crystals; Other Solid; Dry Powder; Liquid
White crystals that change to red on exposure to light and air; [CHEMINFO]
WHITE CRYSTALS. TURNS RED ON EXPOSURE TO AIR.
Colorless or white colored needles that turn red or purple in air.

3.2.2 Color / Form

WHITE CRYSTALS BECOMING RED ON EXPOSURE TO AIR
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
Colorless needles
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. 3rd ed. New York, NY: Van Nostrand Reinhold Co., 1996., p. 1531
RHOMBIC CRYSTALS FROM ALCOHOL
Weast, R.C. (ed.) Handbook of Chemistry and Physics. 67th ed. Boca Raton, FL: CRC Press, Inc., 1986-87., p. C-422
COLORLESS RHOMBIC NEEDLES
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2476
Dark oxidation products /are/ present in compound exposed to moist air.
ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine p.2 (1979)

3.2.3 Boiling Point

540 to 543 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
284-287 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
540-543 °F

3.2.4 Melting Point

145 to 147 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
145-147 °F
62-63 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255

3.2.5 Flash Point

280 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
187 °C c.c.
280 °F

3.2.6 Solubility

less than 1 mg/mL at 66 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
In water, 2.38X10+5 mg/l at 20 deg
Stephen H, Stephen T; Solubilities of Inorganic and Organic Compounds. New York, NY (1963)
Solubility in water: soluble

3.2.7 Density

1.0696 at 136 °F (NTP, 1992) - Denser than water; will sink
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.0096 g/cu m at 58 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-37
Density = 1.139
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
1.14 g/cm³
1.0696 at 136 °F

3.2.8 Vapor Density

3.7 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Relative vapor density (air = 1): 3.7
3.7

3.2.9 Vapor Pressure

1 mmHg at 211.6 °F ; 0.0018 mmHg at 77 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
0.0018 [mmHg]
1 MM HG @ 99.8 °C
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 111 (1978)
Vapor pressure, Pa at 99.8 °C: 133
1 mmHg at 211.6 °F, 0.0018 mmHg at 77 °F

3.2.10 LogP

log Kow = -0.33
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 21
-0.33

3.2.11 Stability / Shelf Life

UNSTABLE IN AIR
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 672

3.2.12 Autoignition Temperature

1040 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
560 °C

3.2.13 Decomposition

WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF NITROGEN OXIDES.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2653

3.2.14 Refractive Index

INDEX OF REFRACTION: 1.6339 AT 58 °C/D
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-37

3.2.15 Dissociation Constants

pKa = 4.98 at 25 °C (conjugate acid)
Perrin DD; Dissociation constants of organic bases in aqueous solution. IUPAC chemical data series. Buttersworth London (1965)
pKa1 = 2.65; pKa2 = 4.88 at 25 °C
Dean, J.A. Handbook of Organic Chemistry. New York, NY: McGraw-Hill Book Co., 1987., p. 8-46

3.2.16 Kovats Retention Index

Semi-standard non-polar
1303

3.2.17 Other Experimental Properties

DIPOLE MOMENT 1.79
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
Specific gravity = 1.07 at 58/4 °C
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. 3rd ed. New York, NY: Van Nostrand Reinhold Co., 1996., p. 1531

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Nitrogen Compounds -> Amines, Aromatic

3.4.1 Cosmetics

Cosmetic ingredients (m-Phenylenediamine) -> CIR (Cosmetic Ingredient Review)

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
NMR: 458 (Varian Associates NMR Spectra Catalogue)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60D
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
P23954
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Chem Service, Inc., West Chester, Pennsylvania
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.1.3 15N NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker WH-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI RMU-7M
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

108 99.99

80 67.51

81 43.62

28 18.66

53 15.82

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License
CC BY-NC-SA
2 of 7
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NIST Number
374679
Library
Main library
Total Peaks
59
m/z Top Peak
108
m/z 2nd Highest
80
m/z 3rd Highest
81
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4.2.2 MS-MS

NIST Number
1054295
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
109.076
Total Peaks
6
m/z Top Peak
92.2
m/z 2nd Highest
81.2
m/z 3rd Highest
67.2
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4.2.3 LC-MS

1 of 8
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Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
10 V
Precursor m/z
109
Precursor Adduct
[M+H]+
Top 5 Peaks

109.1 999

55.1 142

60 60

41.1 46

92.1 44

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License
CC BY-NC-SA
2 of 8
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
20 V
Precursor m/z
109
Precursor Adduct
[M+H]+
Top 5 Peaks

92.1 999

109.1 944

60.1 84

64.9 62

107.9 45

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License
CC BY-NC-SA

4.2.4 Other MS

1 of 4
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Authors
EPA CCTE and Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Precursor m/z
109.0760247
Precursor Adduct
[M+H]+
Top 5 Peaks

109.076025 999

92.049476 326

65.038577 67

108.0682 23

93.057301 23

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License
CC BY
2 of 4
View All
Authors
EPA CCTE and Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
109.0760247
Precursor Adduct
[M+H]+
Top 5 Peaks

65.038577 999

39.022927 864

80.049476 173

66.046402 120

93.057301 119

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License
CC BY

4.3 UV Spectra

MAX ABSORPTION (CYCLOHEXANE): 240 NM (LOG E= 3.85) SHOULDER; 293 NM (LOG E= 3.42)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-156
UV: 1813 (Sadtler Research Laboratories Spectral Collection)
Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I and II. Boca Raton, FL: CRC Press Inc. 1985., p. V1 166

4.4 IR Spectra

IR Spectra
IR: 6522 (Sadtler Research Laboratories Prism Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
CAPILLARY FILM
Source of Spectrum
SCHOLL
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Source of Sample
Aldrich
Catalog Number
420751
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Sample
Aldrich
Catalog Number
P23954
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
P23954
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

The absorption of m-phenylenediamine ... through dog skin, was studied by determining its concentration in the blood. ... After the gel containing 1.5 g of m-phenylendiamine had been applied to the skin, the m-phenylenediamine concentration in the blood rose quickly. In one hour, it approached the level which was maintained through /to/ the last hour of the dermal contact. ... Three hours after the m-phenylenediamine had been washed off the skin, no detectable concentration was found in the blood.
Kiese M et al; Toxicol Appl Pharm 12: 495-507 (1968)
After the /dog abdominal/ skin was washed, m-phenylenediamine concentration in the blood was observed to decline more rapidly than was the case with p-phenylenediamine and 2,5-diaminotoluene.
Kiese M et al; Toxicol Appl Pharm 12: 495-507 (1968)
META-PHENYLENEDIAMINE IS EXCRETED RAPIDLY, UNCHANGED, WITH LITTLE ABSORPTION.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 119 (1978)
. Groups of seven male Wistar rats were dermally exposed for 24 hr to 556 mumol (14)C-meta-phenylenediamine (MPD; 1,3-diaminobenzene) in either aqueous solution (Group 2) or 4% hydrogen peroxide (Group 3). The percutaneous absorption and the amount of non-excreted radioactivity were significantly higher in Group 2 rats. Radioactivity associated with DNA purified from the liver and kidneys was demonstrated. Urine was the principal route of excretion, especially in Group 2 rats. Rats in Group 3 excreted significantly more MPD in the faeces than did Group 2 rats. Urinary excretion of material that constituted two of the peaks in the high-performance liquid chromatogram demonstrated first-order elimination kinetics. ...
Lam HR, Bisgaard HC; Food Chem Toxicol 27 (11): 741-50 (1989)

7.2 Metabolism / Metabolites

m-Phenylenediamine is metabolized in the liver ... as well as being excreted unchanged in the urine.
ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamines p.5 (1979)
Groups of seven male Wistar rats were dermally exposed for 24 hr to 556 mumol (14)C-meta-phenylenediamine (MPD; 1,3-diaminobenzene) in either aqueous solution (Group 2) or 4% hydrogen peroxide (Group 3). ... Three N-acetylated metabolites (N-acetyl-1,3-diaminobenzene, N,N'-diacetyl-2,4-diaminophenol and N,N-diacetyl-1,3-diaminobenzene) accounted for 49 and 37% of the urinary excretion of group 2 and 3 rats, respectively, indicating that such metabolites represent important pathways in the metabolism of MPD. Minor exception of at least one highly hydrophilic, unidentified metabolite of MPD was demonstrated. ...
Lam HR, Bisgaard HC; Food Chem Toxicol 27 (11): 741-49 (1989)

7.3 Mechanism of Action

In all experiments concerning the absorption of m-phenylenediamine through the skin, increases in ferrihemoglobin (methemoglobin) concentration of various degrees were observed. ... The delay of the ferrihemoglobin formation /indicates that/ a transformation of the m-phenylenediamine is necessary for ferrihemoglobin formation. ... 6 mg of m-phenylenediamine/kg injected intravenously, ... took more than two hours before the formation of ferrihemoglobin had attained its maximum speed.
Kiese M et al; Toxicol Appl Pharm 12: 495-507 (1968)

8 Use and Manufacturing

8.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: m-Phenylenediamine
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used to make diisocyanates for the production of polyurethane foams and other resins and polymers; Also used as a corrosion inhibitor, curing agent, photographic developer, and intermediate for other chemical products; [CHEMINFO] Used to make dyes, to develop dyes, to dye hair, and to cure epoxy resins; [ACGIH]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
Industrial Processes with risk of exposure

Plastic Composites Manufacturing [Category: Industry]

Photographic Processing [Category: Other]

Dressing Hair [Category: Other]

MFR DYES; RUBBER CURING AGENTS; ION EXCHANGE RESINS, DECOLORIZING RESINS, FORMALDEHYDE CONDENSATES; RESINOUS POLYAMIDES, BLOCK POLYMERS, TEXTILE FIBERS, URETHANES, PETROLEUM ADDITIVES, RUBBER CHEMICALS; IN CORROSION INHIBITORS; IN PHOTOGRAPHY; AS REAGENT FOR GOLD & BROMINE
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
Dyestuff manufacture, detection of nitrite, textile developing agent, laboratory reagent, vulcanizing agent.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 899
IT IS ... EMPLOYED AS CURING AGENT TO HARDEN EPOXY RESINS USED IN CASTING & PLASTIC TOOLING, LAMINATING APPLICATIONS & IN ADHESIVES. IT IS ADDED TO ISOPHTHALOYL CHLORIDE TO PRODUCE POLY-META-PHENYLENE ISOPHTHALAMIDE RESIN, A POLYAMIDE FIBER (NOMEX) USED IN HIGH-TEMP APPLICATIONS, EG PROTECTIVE CLOTHING ...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 114 (1978)
... CAN BE USED FOR PRODN OF OVER 140 DYES, 37 OF WHICH ARE BELIEVED TO HAVE COMMERCIAL ... SIGNIFICANCE. ... THESE DYES ARE USED TO COLOR VARIOUS TEXTILE FIBERS & OTHER MATERIALS, EG, LEATHER, PAPER, POLISHES, SPIRIT INKS ... ALSO USED AS DIRECT DYE DEVELOPER TO OBTAIN BLACK, BLUE & BROWN SHADES ... AND IT IS INCL IN HAIR-DYE FORMULATIONS TO PRODUCE BROWN, GOLDEN-BLOND, BLUE & GRAY SHADES ON THE HAIR.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 114 (1978)
For more Uses (Complete) data for 1,3-BENZENEDIAMINE (11 total), please visit the HSDB record page.

8.1.1 Use Classification

Hazard Classes and Categories ->

8.1.2 Industry Uses

  • Paint additives and coating additives not described by other categories
  • Processing aids, not otherwise listed
  • Hardener
  • Other
  • Intermediate
  • Intermediates
  • Flame retardant
  • Adhesion/cohesion promoter

8.1.3 Consumer Uses

  • Paint additives and coating additives not described by other categories
  • Adhesion/cohesion promoter

8.1.4 Household Products

Household & Commercial/Institutional Products

Information on 1 consumer products that contain 3-Phenylenediamine in the following categories is provided:

• Personal Care

8.2 Methods of Manufacturing

PREPN: PREPARED BY THE REDUCTION OF M-DINITROBENZENE: KUHN, US PATENT 2,768,209 (1956 TO RINGWOOD); FAUST, J PRAKT CHEM 6, 14 (1958); NEILSON ET AL, J CHEM SOC 1962, 371; TALLEE, PELTIER, COMPT REND 259, 400 (1964).
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
PREPN: REDUCTION OF META-DINITROBENZENE OR NITROANILINE WITH IRON & HYDROCHLORIC ACID. PURIFIED BY CRYSTALLIZATION.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 899

8.3 Impurities

m-Phenylenediamine: purity 99.5% minimum /with the following constituents:/ water-insoluble matter, 0.1% maximum; moisture content, 0.1% maximum; moisture content, 0.1% maximum; dinitrobenzene, 0.1% maximum; p-Phenylenediamine, 500 mg/kg maximum; o-Phenylenediamine, 200 mg/kg maximum.
ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine (Enclosure #1) (1979)
In Japan, m-phenylenediamine is available with a minimum purity of 98.5%. ... Dinitrobenzene and phenylenediamine isomers are /found/ as impurities.
ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine (Enclosure #1) (1979)

8.4 Formulations / Preparations

GRADES: TECHNICAL; 99% MIN PURITY.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 899

8.5 U.S. Production

Aggregated Product Volume

2019: 10,000,000 - <50,000,000 lb

2018: 10,000,000 - <50,000,000 lb

2017: 10,000,000 - <50,000,000 lb

2016: 10,000,000 - <50,000,000 lb

(1977) AT LEAST 4.54X10+7 GRAMS
SRI
(1983) < 20,000,000 lb (estimate)
ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine p.2 (1979
Production figures for m-phenylenediamine are not available. ... From an analysis of two of its principle uses ... infer that production for the 1976-1977 time period could have been as high as 6 million pounds.
ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine p.2 (1979)

8.6 U.S. Imports

(1977) 8.31X10+6 GRAMS (PRINCPL CUSTMS DISTS)
SRI
0-135,700 lb (1976-1982)
TRDB/USEPA; Technical Support Document (Draft) Phenylenediamines p.11 (1984)

8.7 General Manufacturing Information

Industry Processing Sectors
  • Plastics Product Manufacturing
  • Synthetic Dye and Pigment Manufacturing
  • All Other Chemical Product and Preparation Manufacturing
  • Synthetic Rubber Manufacturing
  • Plastics Material and Resin Manufacturing
  • Organic Fiber Manufacturing
  • Paint and Coating Manufacturing
  • All Other Basic Organic Chemical Manufacturing
EPA TSCA Commercial Activity Status
1,3-Benzenediamine: ACTIVE

8.8 Sampling Procedures

META-PHENYLENEDIAMINE IS COLLECTED ON SULFURIC COATED SILICA GEL AS SULFATE SALT. SALT IS THEN RINSED FROM GEL, DIAZOTIZED & THEN COUPLED TO FORM AN AZO DYE WHICH IS MEASURED SPECTROPHOTOMETRICALLY AT 520 NM.
WILLIAMS NJ & VAN HOOK SJ; REPORT; ISS Y/DK-231 (1979) 17 PP.
In Air: by aspiration through ethanol ...
Simonov VA et al; Gig Sant 36: 55 (1971) as cited in ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine p.116 (1979)

9 Identification

9.1 Analytic Laboratory Methods

. A RAPID COLORIMETRIC METHOD DETERMINING META-PHENYLENEDIAMINE IN AIR REVEALED A SENSITIVITY OF O.6 UG M-PHENYLENEDIAMINE IN SAMPLE VOL.
SIMONOV ET AL; GIG SANIT 35 (5): 99-100 (1970)
METHOD TO DETERMINE PRESENCE OF M-PHENYLENEDIAMINE IN WATER IS BY THIN-LAYER CHROMATOGRAPHY.
KAZARINOVA ET AL; GIG SANIT 11: 61-3 (1974)
Ultra-violet spectrophotometry has been used to analyze ... /m-phenylenediamine/ in air by aspiration through ethanol and absorbance measurement.
Simonov VA et al; Gig Sant 36: 55 (1971) as cited in ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine p.116 (1979)
Paper chromatography, using six different solvent systems and fifteen spray reagents and ultra-violet light, has been used to separate m-phenylenediamine from other aminobenzene derivatives.
Reio L; J Chromat 47: 60 (1970) as cited in ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine p.116 (1979)
For more Analytic Laboratory Methods (Complete) data for 1,3-BENZENEDIAMINE (10 total), please visit the HSDB record page.

9.2 Clinical Laboratory Methods

Aromatic primary amines or compounds yielding them on reduction or hydrolysis can be detected by their color reaction at /a/ pH /of/ 3 with and N-substituted p-aminophenols. ... Sample preparations from tablets ... blood, and urine are described. Beer's law limits, molar absorptivities, and standard deviations are tabulated for 40 pharmaceuticals. ... /Aromatic primary amines/
Sastry CSP et al; Indian Drugs 21(4): 145-152 (1984)

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 6
View All
Pictogram(s)
Acute Toxic
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H301+H311+H331 (29.8%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H341 (99.7%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H400 (96.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 373 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

Skin Sens. 1 (100%)

Eye Irrit. 2A (100%)

Acute Tox. 3 (100%)

Muta. 2 (99.7%)

Aquatic Acute 1 (96.5%)

Aquatic Chronic 1 (100%)

Germ cell mutagenicity - category 2

Acute toxicity - category 3

Acute toxicity - category 3

Acute toxicity - category 3

Skin sensitisation - category 1

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 1

Eye irritation - category 2A

10.1.3 Health Hazards

SYMPTOMS: Symptoms of exposure to this chemical may include skin sensitization reactions, eye irritation and injury, skin irritation, dermatitis, blackened skin and bronchial asthma. Other symptoms may include allergic skin reactions, irritation of the mucous membranes, nose, throat and lungs, coughing, burning sensation, runny nose, sore throat, methemoglobinemia, cyanosis, headache, dizziness, drowsiness, mental confusion, pulmonary edema, kidney and liver damage, central nervous system effects and conjunctivitis. Eye contact may cause discomfort, tearing, blurring of vision, reddening, partial clouding of the cornea and swelling of the eye and surrounding tissue. Dysuria and eosinophiluria may also occur. Exposure may also result in respiratory tract irritation.

ACUTE/CHRONIC HAZARDS: This compound is harmful if inhaled, swallowed or absorbed through the skin. It causes irritation of the eyes, skin, mucous membrane and respiratory tract. When heated to decomposition, this compound emits irritating and/or toxic gases and fumes of carbon monoxide, carbon dioxide and oxides of nitrogen. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.1.4 Fire Hazards

This chemical is combustible. Dust may form explosive mixtures in air (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

10.1.5 Hazards Summary

In acute studies at lethal doses (650 mg/kg), animals have tremors, convulsions, cyanosis, and methemoglobinemia. In subchronic studies, rats have increased liver weights. Critical Effects are irritation; liver; Confirmed Animal Carcinogen with Unknown Relevance to Humans; [ACGIH] Danger of skin sensitization; [MAK]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.

10.1.6 Fire Potential

FIRE POINT: 175 °C.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
Combustible when exposed to heat or flame.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2653

10.1.7 Skin, Eye, and Respiratory Irritations

STRONG IRRITANT TO SKIN. TOXIC BY ... INHALATION.
Hawley, G.G. The Condensed Chemical Dictionary. 10th ed. New York: Van Nostrand Reinhold Co., 1981., p. 672

10.2 First Aid Measures

Inhalation First Aid
Fresh air, rest. Refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth. Refer for medical attention .

10.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.3 Fire Fighting

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

SMALL FIRE: Dry chemical, CO2 or water spray.

LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Use water spray, powder.

10.4 Accidental Release Measures

10.4.1 Isolation and Evacuation

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

10.4.2 Spillage Disposal

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

10.4.3 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Recommendable method: Incineration. Peer-review: (Peer-review conclusions of an IRPTC expert consultation (May 1985))
United Nations. Treatment and Disposal Methods for Waste Chemicals (IRPTC File). Data Profile Series No. 5. Geneva, Switzerland: United Nations Environmental Programme, Dec. 1985., p. 229

10.5 Handling and Storage

10.5.1 Nonfire Spill Response

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

10.5.2 Safe Storage

Separated from strong oxidants and food and feedstuffs. Keep in the dark. Well closed.

10.5.3 Storage Conditions

KEEP WELL CLOSED & PROTECTED FROM LIGHT.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255

10.6 Exposure Control and Personal Protection

10.6.1 Threshold Limit Values (TLV)

0.1 [mg/m3]
8 hr Time Weighted Avg (TWA): 0.1 mg/cu m. /m-Phenylenediamine/
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH, 2008, p. 47
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed three times the TLV-TWA for no more than a total of 30 min during a work day, and under no circumstances should they exceed five times the TLV-TWA, provided that the TLV-TWA is not exceeded. /m-Phenylenediamine/
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH, 2008, p. 47
A4; Not classifiable as a human carcinogen. /m-Phenylenediamine/
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH, 2008, p. 47
0.1 mg/m
TLV-TWA (Time Weighted Average)
0.1 mg/m³ [1988]

10.6.2 Occupational Exposure Limits (OEL)

MAK (Maximale Arbeitsplatz Konzentration)
skin absorption (H); sensitization of skin (SH); carcinogen category: 3

10.6.3 Inhalation Risk

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

10.6.4 Effects of Short Term Exposure

The substance is irritating to the eyes and skin. The substance may cause effects on the kidneys and blood. This may result in renal failure and the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

10.6.5 Effects of Long Term Exposure

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the kidneys. This may result in renal failure.

10.6.6 Personal Protective Equipment (PPE)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE. Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

10.6.7 Preventions

Fire Prevention
NO open flames.
Exposure Prevention
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Inhalation Prevention
Use local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear safety goggles, face shield or eye protection in combination with breathing protection.
Ingestion Prevention
Do not eat, drink, or smoke during work.

10.7 Stability and Reactivity

10.7.1 Air and Water Reactions

Soluble in water [Merck].

10.7.2 Reactive Group

Amines, Aromatic

10.7.3 Reactivity Profile

1,3-PHENYLENEDIAMINE an aromatic amine, neutralizes acids, acid chlorides, acid anhydrides and chloroformates in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Incompatible with oxidizing agents (NTP, 1992).
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.8 Transport Information

10.8.1 DOT Emergency Guidelines

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Phenylenediamines/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Phenylenediamines/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Phenylenediamines/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Phenylenediamines/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
For more DOT Emergency Guidelines (Complete) data for 1,3-BENZENEDIAMINE (8 total), please visit the HSDB record page.

10.8.2 Shipping Name / Number DOT/UN/NA/IMO

UN 1673; Phenylenediamine, meta, solid; m-Phenylenediamine

10.8.3 Standard Transportation Number

49 403 67

10.8.4 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2 (7/1/96)
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
IATA. Dangerous Goods Regulations. 38th ed. Montreal, Canada and Geneva, Switzerland: International Air Transport Association, Dangerous Goods Board, January, 1997., p. 197
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.6201 (1988)

10.8.5 DOT Label

Poison

10.8.6 Packaging and Labelling

Do not transport with food and feedstuffs.

10.8.7 EC Classification

Symbol: T, N; R: 23/24/25-36-43-50/53-68; S: (1/2)-28-36/37-45-60-61

10.8.8 UN Classification

UN Hazard Class: 6.1; UN Pack Group: III

10.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1,3-Benzenediamine
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
1,3-Phenylenediamine: Does not have an individual approval but may be used under an appropriate group standard

10.9.1 TSCA Requirements

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3-Benzenediamine is included on this list.
40 CFR 716.120 (7/1/96)
Manufacturers and processors of meta-phenylenedimine are required to conduct health efffects, chemical fate and environmental effects testing under TSCA section 4.
40 CFR 799.3300 (7/1/96)

10.10 Other Safety Information

Chemical Assessment

IMAP assessments - 1,3-Benzenediamine: Human health tier II assessment

Evaluation - Phenylenediamines

10.10.1 Special Reports

ITC/USEPA; Information Review #102 (Draft) m-Phenylenediamine (1979)
TRDB/USEPA; Technical Support Document (Draft) Phenylenediamines (1984)
NIOSH: Current Intelligence Bulletin 2,4-Diaminoanisole #19 (1978)
TSCA CHIPs present a preliminary assessment of 1,4-Benzenediamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404 or (800) 424-9065).
USEPA; PHENYLENEDIAMINES; RESPONSE TO INTERAGENCY TESTING COMMITTEE; FED REGIST 47(5) 973 (1982). EVIDENCE IS GIVEN SUPPORTING TESTING OF THE CLASS OF COMPOUNDS PHENYLENEDIAMINES FOR THEIR TOXIC EFFECTS ON HUMAN HEALTH AND THE ENVIRONMENT. THE RESULTS OF TOXICITY TESTING OF 22 COMPOUNDS ARE TABULATED AS ARE THE EFFECTS FOR WHICH TESTING IS BEING CONSIDERED FOR 13 COMPOUNDS, AND THE USES OR POTENTIAL USES OF 47 PHENYLENEDIAMINES.

11 Toxicity

11.1 Toxicological Information

11.1.1 EPA IRIS Information

Toxicity Summary
EPA IRIS Summary PDF (Update: Jan-31-1987 )
Critical Effect Systems
Hepatic
Reference Dose (RfD), chronic
6 x 10 ^-3 mg/kg-day

11.1.2 RAIS Toxicity Values

Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.006
Oral Chronic Reference Dose Reference
IRIS Current
Oral Subchronic Chronic Reference Dose (RfDos) (mg/kg-day)
0.06
Oral Subchronic Chronic Reference Dose Reference
HEAST Current

11.1.3 Evidence for Carcinogenicity

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. S7 70 (1987)
A4; Not classifiable as a human carcinogen. /m-Phenylenediamine/
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH, 2008, p. 47

11.1.4 Carcinogen Classification

IARC Carcinogenic Agent
meta-Phenylenediamine
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs

Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

11.1.5 Exposure Routes

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

11.1.6 Symptoms

Inhalation Exposure
Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.
Skin Exposure
MAY BE ABSORBED! Redness. Further see Inhalation.
Eye Exposure
Redness. Pain.
Ingestion Exposure
See Inhalation.

11.1.7 Target Organs

Hepatic

11.1.8 Adverse Effects

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

ACGIH Carcinogen - Not Classifiable.

11.1.9 Acute Effects

11.1.10 Interactions

Paraoxon (diethyl-p-nitrophenylphosphate) is the toxic, but non-mutagenic metabolite of the organophosphorus ester insecticide parathion. ... A mutagenic synergy when paraoxon was incubated with plant activated m-phenylenediamine (mPDA) or with direct acting 2-acetoxyacetylaminofluorene ... and Salmonella typhimurium tester strains /was discovered/. ... /With/ non-toxic concn of plant activated mPDA and paraoxon a 10-fold incr in the mutant yield of S. typhimurium was observed. The mutagenicity of the plant activated mPDA product required that O-acetyltransferase (OAT) be expressed by the S. typhimurium tester strain. However, the paraoxon dependent mutagenic synergy was observed using the direct acting arylamine metabolite, 2AAAF, with strains YG1024, TA98 and TA98/1,8-DNP6 regardless of their OAT activity. This mutagenic synergy is dependent upon the presence of an activated acetylated form of the arylamine. The data presented here demonstrate that this mutagenic synergy is limited to paraoxon and not to the parent compound (parathion) or to a major metabolite of parathion (p-nitrophenol).
Gichner T, et al; Environ Mutagen 27 (1): 59-66 (1996)

11.1.11 Antidote and Emergency Treatment

For immediate first aid: Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Organic bases, amines, and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 168
For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... Cover skin burns with sterile dressings after decontamination ... . /Organic bases, amines, and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 168

11.1.12 Human Toxicity Excerpts

WORKERS ... EXAMINED. ... AGES RANGED FROM 30-50 YR, & DURATION OF POTENTIAL EXPOSURE WAS 5-10 YR. SOME ... COMPLAINED OF DYSURIA. ... THEY DISPLAYED EOSINOPHILURIA ... CYSTOSCOPY DEMONSTRATED EDEMA OF MUCOSA, POLYPOUS SWELLINGS & INFILTRATION OF AREA OF TRIANGLE & CERVIX OF URINARY BLADDER ...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 119 (1978)
EFFECTS OBSERVED IN PROFESSIONALLY EXPOSED PERSONS (1-2 UG/L) WERE HYPERREFLEXIA, HYPOREFLEXIA, ANISOREFLEXIA, SKIN HYPERESTHESIA, & PATHOLOGICAL CHANGES IN KIDNEYS & LIVER.
KACHALAI ET AL; FARMAKOL TOKSIKOL (KIEV) 8: 180-3 (1973)
The p-form is more toxic and a stronger irritant than the o- and m-isomers.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2654
Suspected carcinogen with experimental tumorigenic and teratogenic data. Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Mildly toxic by skin contact. Mutation data reported.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2653
The promutagenic arylamines, m-phenylenediamine (mPDA) and 2-aminofluorene (2-AF), were evaluated for their genotoxicity in ... in human lymphocytes. ...These agents were assayed with and without TXlMX plant activation mix. ... Using the alkaline single cell gel/Comet assay, both mPDA and 2-AF directly induced DNA damage in human lymphocytes. This effect was reduced when the human cells were treated with the arylamine plus TXlMX. ... However, at concentrations over 80 microM, 2-AF was toxic to lymphocytes. This toxic response was eliminated by incubation with TXlMX. ... mPDA and 2-AF plant activated products had a reduced genotoxic potency in human lymphocytes.
Plewa MJ, et al; Environ Mol Mutagen 26 (2): 171-7 (1995)

11.1.13 Non-Human Toxicity Excerpts

21 ENVIRONMENTAL AROMATIC AMINES OR DERIV WERE TESTED FOR LONG TERM TOXICITY OR CARCINOGENICITY BY DIETARY ADMIN TO MALE CHARLES RIVER RATS & MALE & FEMALE HAM/ICR MICE. M-PHENYLENEDIAMINE WAS INACTIVE.
WEISBURGER ET AL; J ENVIRON TOXICOL 2 (2): 325-56 (1978) (RECD 1979)
... WISTAR-KING RATS ... TREATED ... WITH META-PHENYLENEDIAMINE AT A DOSE OF 9 OR 18 MG/KG BODY WEIGHT ... CMPD ... INJECTED SUBCUTANEOUSLY INTO THE BACK ON ALTERNATE DAYS FOR 5 MO IN HIGHER DOSE GROUPS & FOR 11 MO IN LOWER DOSE GROUPS. ... FIBROSARCOMAS WERE PRODUCED IN ONE RAT IN THE GROUP TREATED WITH 9 MG/KG ... NO TUMORS WERE FOUND IN ANY OF THE OTHER GROUPS NOR IN THE CONTROL GROUPS. OBSERVATION PERIOD NOT SPECIFIED (SARUTA, 1962).
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 117 (1978)
ORAL ADMIN @ 5.6-28 MG/KG/DAY TO RATS FOR 3-4 MO AFFECTED CNS & DETOXIFYING ACTIVITY OF LIVER, DECR URINARY EXCRETION OF HIPPURIC ACID & INCR LEVEL OF SH-GROUPS IN BLOOD & LIVER. WHEN APPLIED AT 28 MG/KG TO THE SKIN, IT CAUSED DERMATITIS.
KACHALAI ET AL; FARMAKO TOKSIKOL (KIEV) 8: 180-3 (1973)
NO DOMINANT LETHALS WERE INDUCED IN CHARLES RIVER RATS INJECTED IP 3 TIMES WEEKLY FOR 8 WK WITH 20 MG/KG BODY WT META-PHENYLENEDIAMINE BEFORE MATING (NO POSITIVE CONTROL SUBSTANCE WAS TESTED).
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 119 (1978)
For more Non-Human Toxicity Excerpts (Complete) data for 1,3-BENZENEDIAMINE (21 total), please visit the HSDB record page.

11.1.14 Non-Human Toxicity Values

NOAEL rat 6 mg/kg
TRDB/USEPA; Technical Support Document (Draft) Phenylenediamines p.54 (1984)
LD50 Rat oral 650 mg/kg
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255
LD50 Rat ip 283 mg/kg
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1255

11.1.15 TSCA Test Submissions

m-Phenylenediamine (CAS # 108-45-2) commercial grade, was evaluated for dermal carcinogenicity in 24-month skin-painting study with male and female C3H and C57BL/6 mice (40 and 20/sex/group, respectively) exposed daily to doses of 0.6 or 3.0 mg/day. Mice were sacrificed for histologic evaluation at a rate and time determined by incidence of tumor-bearing mice during the course of treatment. Study lethalities and survivors killed at termination of study were necropsied for examination of major organ systems and the brain to determine degree of substance absorption and potential systemic toxicity. Diagnosis of any gross pathology upon these analyses were confirmed histologically. In 24-month study, mortality was significantly higher in the 3 mg, B6 males, however no increased risk of skin tumors was established for either strain or sex of mice in association with treatment.
CIBA GEIGY CORP; Carcinogenicity of bis(2,3-Epoxycyclopentyl)ether, 2,2-bis(p-glycidyloxyphenyl)propane and m-Phenylenediamine in C3H and C57BL/6 Inbred Male and Female Mice; EPA Doc No. 88-920008206; Fiche No. OTS0555024
meta-Phenylenediamine (CAS # 108-45-2) was evaluated for clastogenic effects in male and female Crl:CDBR mice (5-6/sex/group) following gavage dosing (2 doses, 24 hours apart) at concentrations of 0, 16, 33, and 65 mg/kg bodyweight. Five animals/sex/group were sacrificed for harvest of femur bone marrow and 1000 polychromatic erythrocytes/animal at 24 hours (all treatment groups) and 48 hours (0 and 65 mg/kg/day groups) after a second dose. Bone marrow smears were analyzed for treatment-related incidence of micronuclei in polychromatic erythrocytes. At all dose levels, in vivo observations included lethargy, half-closed eyes, and labored and/or rapid breathing. A solitary 65 mg/kg/day male found dead 24 hours after a second dose comprised the study mortality and weight loss in 33 and 65 mg/kg/day treatment groups was statistically significant. Upon cytogenetic evaluation, there was no statistically significant increase in micronucleated polychromatic erythrocytes in any treatment group relative to vehicle control (deionized water). The only statistically significant (p < 0.05; Dunnett's test) finding from all bone marrow smears was a reduction in young, polychromatic erythrocytes.
E I DUPONT DE NEMOURS & CO; Mouse Bone Marrow Micronucleus Assay of meta-Phenylenediamine; 1/9/91; EPA Doc No. 40-9136484; Fiche No. OTS0533308
m-Phenylenediamine (CAS # 108-45-2) was evaluated for acute oral neurotoxicity in Crl:CDBR rats (12/sex/group) administered single gavage doses of 0, 75, 150, and 300 mg/kg (10 ml/kg in sterile water). Bodyweight, feed consumption, clinical signs, functional observational battery performance, fore-, and hindlimb grip strength, foot splay, and motor activity were assessed prior to treatment (baseline values), and at 1 hour, 24 hours, and 4 days post-treatment. Toxicity was demonstrated at all dose levels and generally to a greater extent in females. Females at the 150 and 300 mg/kg dose level, one and eight rats, respectively, were found dead prior to scheduled sacrifice, death occurring from 2-4 days after treatment. All study lethalities were found with pallor and staining. Significant weight loss within one day of dosing and persisting throughout Day 4 was common to 150 and 300 mg/kg treatment groups, while food consumption was adversely affected in a dose-related manner. A rebounding of food consumption and bodyweights was noted thereafter. Clinical signs were apparent from day of dosing and included dose-related pallor in females, and irregular head movements, coloration of urine and a tip-toe gait in males and females. The functional observational battery revealed significant general malaise, postural changes, and palpebral closure. High-dose females also showed diminished arousal. Measurements of fore- and hindlimb grip strength and foot splay were not indicative of a neurotoxicity at any treatment level. Motor activity was significantly depressed following treatment in all treatment groups relative to control (p
E I DUPONT DE NEMOURS & CO; Acute Oral Neurotoxicity Studies of para, meta and ortho-Phenylenediamine in Rats; 9/14/90; EPA Doc No. 40-9036454; Fiche No. OTS0528739
meta-Phenylenediamine (CAS # 108-45-2) was evaluated for subchronic oral neurotoxicity in male and female Crl:CDBR rats (10/sex/group) administered daily gavage doses of 0, 5, 10, and 20 mg/kg for 90 consecutive days. A functional observational battery and motor activity tests were conducted prior to dosing and at weeks 4, 8, and 13 during treatment. Male rats only exhibited minimal dose-related reductions in both horizontal (10 and 20 mg/kg groups) and vertical motor activity (20 mg/kg group) during treatment weeks 4 and 8 relative to controls. Study authors attributed these findings, which were not statistically significant, to general malaise characterized by lethargy rather than a direct effect of treatment on the central nervous system. Neuropathological evaluation at termination of study yielded no anomalies within the nervous system or skeletal muscle.
E I DUPONT DE NEMOURS & CO; Results from Ongoing Subchronic Neurotoxicity Evaluation Performed on meta-Phenylenediamine; 5/8/92; EPA Doc No. 88-920002361; Fiche No. OTS536413
For more TSCA Test Submissions (Complete) data for 1,3-BENZENEDIAMINE (8 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 US EPA Regional Screening Levels for Chemical Contaminants

Resident Soil (mg/kg)
3.80e+02
Industrial Soil (mg/kg)
4.90e+03
Tapwater (ug/L)
1.20e+02
MCL (ug/L)
1.5E+01(G)
Risk-based SSL (mg/kg)
3.20e-02
Chronic Oral Reference Dose (mg/kg-day)
6.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11.2.2 US EPA Regional Removal Management Levels for Chemical Contaminants

Resident Soil (mg/kg)
1.10e+03
Industrial Soil (mg/kg)
1.50e+04
Tapwater (ug/L)
3.60e+02
MCL (ug/L)
1.5E+01 (G)
Chronic Oral Reference Dose (mg/kg-day)
6.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11.2.3 ICSC Environmental Data

The substance is toxic to aquatic organisms.

11.2.4 Environmental Fate / Exposure Summary

1,3-Benzenediamine may be released to the environment in various waste streams from its production and use in the manufacture of dyes, as a rubber curing agent, in ion-exchange resins, decolorizing resins, formaldehyde condensates, resinous polyamides, block polymers, textile fibers, urethanes, petroleum additives, rubber chemicals, corrosion inhibitors, photography, as a reagent for gold and bromine and as a component of hair-dye formulations. If released to the atmosphere, 1,3-benzenediamine is expected to exist solely as a vapor in the ambient atmosphere based on an extrapolated vapor pressure of 2.1X10-3 mm Hg at 25 °C. Vapor-phase 1,3-benzenediamine is rapidly degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals (estimated half-life 1.9 hours). 1,3-Benzenediamine absorbs light in the environmental spectrum, which suggests a potential for direct photolysis in the environment. If released to soil, 1,3-benzenediamine is expected to have very high mobility based on an estimated Koc of 16. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group; therefore, mobility may be much lower in some soils. 1,3-Benzenediamine is not expected to volatilize from wet or dry soil surfaces, based on an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mol and this compound's extrapolated vapor pressure, respectively. Limited data indicate 1,3-benzenediamine may be resistant to biodegradation in soil. If released into water, volatilization of 1,3-benzenediamine is not expected to occur, based on its estimated Henry's Law constant. 1,3-Benzenediamine may exist partially in the ionized form at environmental pH's based on pKa values of 2.65 and 4.88 at 25 °C. Volatilization of the ionized form is not expected to be an important fate process. The potential for bioconcentration in aquatic organisms is expected to be low based on measured BCF values ranging from 1.3 to 24 in carp. Based on its structure, aromatic amine, 1,3-benzenediamine may adsorb strongly to suspended solids and sediment in water. As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically produced hydroxyl radicals and peroxy radicals (typical half-lives for peroxy radical and hydroxyl radical reactions are on the order of 19 and 30 sunlight hours, respectively). Hydrolysis is not expected to be an important process. Aqueous screening studies indicate 1,3-benzenediamine may be susceptible to biodegradation by acclimated activated sludge. Occupational exposure to 1,3-benzenediamine may occur through inhalation and dermal contact with this compound at workplaces where 1,3-benzenediamine is produced or used. The general population may be exposed to 1,3-benzenediamine via dermal contact with consumer products containing this compound. (SRC)

11.2.5 Natural Pollution Sources

1,3-Benzenediamine is of anthropogenic origin and is not known to be produced by natural sources. (SRC)

11.2.6 Artificial Pollution Sources

1,3-Benzenediamine's production and use in the manufacture of dyes, as a rubber curing agent, in ion-exchange resins, decolorizing resins, formaldehyde condensates, resinous polyamides, block polymers, textile fibers, urethanes, petroleum additives, rubber chemicals, corrosion inhibitors, photography, as a reagent for gold and bromine(1), and as a component of hair-dye formulations(2) may result in its release to the environment through various waste streams(SRC).
(1) Budavari S; The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 12th ed. Whitehouse Station, NJ: Merck and Co Inc p. 1255 (1996)
(2) IARC; Monographs 1972-Present V16 p. 114 (1978)

11.2.7 Environmental Fate

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.33(2) and a recommended regression-derived equation(3), indicates that 1,3-benzenediamine is expected to have very high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5); therefore, mobility may be much lower in some soils(SRC). Volatilization of 1,3-benzenediamine is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), from its extrapolated vapor pressure, 2.1X10-3 mm Hg(6), and measured water solubility, 2.4X10+5 mg/l(7). 1,3-Benzenediamine is not expected to volatilize from dry soil surfaces based on its extrapolated vapor pressure(6). Limited biodegradation data indicate 1,3-benzenediamine may be resistant to biodegradation in soil; soil microflora did not cleave the benzene ring of 1,3-benzenediamine in 64 days(8).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR (consult ed) Washington, DC: Amer Chem Soc p. 21 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9 (1990)
(4) Bollag JM et al; J Agric Food Chem 26: 1302-1306 (1978)
(5) Adrian P et al; Toxicol Environ Chem 20-21: 109-120 (1989)
(6) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY,NY: Hemisphere Pub Corp (1989)
(7) Stephen H, Stephen T; Solubilities of Inorganic and Organic Compounds. NY,NY (1963)
(8) Alexander M, Lustigman BK; J Agric Food Chem 14: 410-3 (1966)
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.33(2) and a recommended regression-derived equation(3), indicates that 1,3-benzenediamine is not expected to adsorb to suspended solids and sediment in water(SRC). However, aromatic amines are recognized as having a strong affinity to organic carbon, suggesting that this compound may bind strongly to suspended organic material in water(4,5). 1,3-Benzenediamine is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 2.1X10-3 mm Hg(6), and measured water solubility, 2.4X10+5 mg/l(7). 1,3-Benzenediamine may exist partially in the ionized form at environmental pH's based on pKa values of 2.65 and 4.88 at 25 °C(8). Volatilization of the ionized form is not expected to be an important fate process(SRC). According to a classification scheme(9), BCF values of 1.3 to 4.6 and <1.6 to 24 measured for 1,3-benzenediamine in carp at 2 and 0.2 mg/l, respectively(10), suggest that bioconcentration in aquatic organisms is low(SRC). 1,3-Benzenediamine in the water column may be susceptible to significant photooxidation via hydroxyl and peroxy radicals; half-lives for these photooxidations may be on the order of 19-30 sunlight hours(11). Aqueous screening studies indicate 1,3-benzenediamine may be susceptible to microbial degradation(SRC); 60% degradation was observed after 5 days using an acclimated activated sludge inoculum(12). 1,3-Benzenediamine was reported to be toxic to 3 unacclimated sludges at concns greater than 50 ppm(13).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR (consult ed) Washington,DC: Amer Chem Soc p. 21 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9, 5-4, 5-10, 15-1 to 15-29 (1990)
(4) Bollag JM et al; J Agric Food Chem 26: 1302-1306 (1978)
(5) Adrian P et al; Toxicol Environ Chem 20-21: 109-120 (1989)
(6) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY,NY: Hemisphere Pub Corp (1989)
(7) Stephen H, Stephen T; Solubilities of Inorganic and Organic Compounds. NY,NY (1963)
(8) Dean JA; Handbook of Organic Chemistry, NY,NY: McGraw-Hill, Inc p. 8-46 (1987)
(9) Franke C et al; Chemosphere 29: 1501-14 (1994)
(10) Chemicals Inspection and Testing Institute; Biodegradation and Bioaccumulation Data of Existing Chemicals Based on the CSCL Japan. Japan Chemical Industry Ecology-Toxicology and Information Center. ISBN #4-89074-101-1 p. 3-28 (1992)
(11) Mill T, Mabey W; p. 208-11 in Environmental Exposure from Chemicals Vol. I, Neely WR, Blau GE eds Boca Raton,FL: CRC Press (1985)
(12) Pitter P; Water Res 10: 231-5 (1976)
(13) Marion CV, Malaney GW; Eng Bull Purdue Univ Eng Ext Ser pp. 297-308 (1964)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-benzenediamine, which has an extrapolated vapor pressure of 2.1X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-benzenediamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 1.9 hours(3,SRC). 1,3-Benzenediamine absorbs light in the environmental spectrum(4), which suggests a potential for direct photolysis in the environment(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY,NY: Hemisphere Pub Corp (1989)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Sadtler NA; Sadtler Standard Spectra. Philadelphia,PA: Sadtler Research Lab 1813 UV Spectra

11.2.8 Environmental Biodegradation

1,3-Benzenediamine was observed to degrade 60% after 5 days at concn levels of 25 to 30 ppm using an acclimated activated sludge inoculum(1). However at 50 ppm 1,3-benzenediamine was reported to be toxic to 3 unacclimated activated sludges(2). Soil microflora did not cleave the benzene ring of 1,3-benzenediamine in 64 days(3). 1,3-Benzenediamine, present at an initial concn of 100 mg/l, reached 2% of its theoretical BOD in 4 weeks using an activated sludge inoculum(4).
(1) Pitter P; Water Res 10: 231-5 (1976)
(2) Marion CV, Malaney GW; Eng Bull Purdue Univ Eng Ext Ser pp. 297-308 (1964)
(3) Alexander M, Lustigman BK; J Agric Food Chem 14: 410-3 (1966)
(4) Chemicals Inspection and Testing Institute; Biodegradation and Bioaccumulation Data of Existing Chemicals Based on the CSCL Japan. Japan Chemical Industry Ecology-Toxicology and Information Center. ISBN #4-89074-101-1 p. 3-28 (1992)

11.2.9 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of 1,3-benzenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.9 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 1,3-Benzenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups to hydrolyze(2). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically produced hydroxyl radicals and peroxy radicals(3); typical half-lives for peroxy radical and hydroxyl radical reactions are on the order of 19 and 30 sunlight hours, respectively(3). 1,3-Benzenediamine absorbs light in the environmental spectra(4), which suggests a potential for direct photolysis in the environment(SRC). Aromatic amines are sensitive to oxidation and crystals of 1,3-benzenediamine turn red on exposure to air(5).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(3) Mill T, Mabey W; p. 208-11 in Environmental Exposure from Chemicals Vol I, Neely WR, Blau GE eds Boca Raton, FL: CRC Press (1985)
(4) Sadtler NA; Sadtler Standard Spectra. Philadelphia, PA: Sadtler Research Lab 1813 UV Spectra
(5) Budavari S; The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 12th ed. Whitehouse Station, NJ: Merck and Co Inc p. 1255 (1996)

11.2.10 Environmental Bioconcentration

An estimated BCF value of 0.33 was calculated for 1,3-benzenediamine(SRC), using an estimated log Kow of -0.33(1) and a recommended regression-derived equation(2). BCF values of 1.3 to 4.6 and <1.6 to 24 were measured for 1,3-benzenediamine in carp at 2 and 0.2 mg/l, respectively(3). According to a classification scheme(4), these BCF values suggest that bioconcentration in aquatic organisms is low(SRC).
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR (consult ed) Washington,DC: Amer Chem Soc p. 21 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 5-4, 5-10 (1990)
(3) Chemicals Inspection and Testing Institute; Biodegradation and Bioaccumulation Data of Existing Chemicals Based on the CSCL Japan. Japan Chemical Industry Ecology-Toxicology and Information Center. ISBN #4-89074-101-1 p. 3-28 (1992)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.11 Soil Adsorption / Mobility

The Koc of 1,3-benzenediamine is estimated as approximately 16(SRC), using a measured log Kow of -0.33(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1,3-benzenediamine is expected to have very high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5); therefore, mobility may be much lower in some soils(SRC).
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR (consult ed) Washington,DC: Amer Chem Soc p. 21 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 23 (1983)
(4) Bollag JM et al; J Agric Food Chem 26: 1302-1306 (1978)
(5) Adrian P et al; Toxicol Environ Chem 20-21: 109-120 (1989)

11.2.12 Volatilization from Water / Soil

The Henry's Law constant for 1,3-benzenediamine is estimated as 1.3X10-9 atm-cu m/mole(SRC) from its extrapolated vapor pressure, 2.1X10-3 mm Hg(1), and water solubility, 2.4X10+5 mg/l(2). This value indicates that 1,3-benzenediamine will be essentially nonvolatile from water surfaces(3,SRC). 1,3-Benzenediamine's Henry's Law constant(1,2,SRC) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 1,3-Benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based on its extrapolated vapor pressure(1). 1,3-Benzenediamine may exist partially in the ionized form at environmental pH's based on pKa values of 2.65 and 4.88 at 25 °C(4). Volatilization of the ionized form is not expected to be an important fate process(SRC).
(1) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng., NY,NY: Hemisphere Pub Corp (1989)
(2) Stephen H, Stephen T; Solubilities of Inorganic and Organic Compounds. NY,NY (1963)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Dean JA; Handbook of Organic Chemistry, NY,NY: McGraw-Hill, Inc p. 8-46 (1987)

11.2.13 Environmental Water Concentrations

DRINKING WATER: 1,3-Benzenediamine was detected in drinking water from an unspecified location(1).
(1) Kraybill HF; J Environ Sci Health C1: 175-232 (1983)

11.2.14 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 29,424 workers (24,818 of these are female) are potentially exposed to 1,3-benzenediamine in the US(1). Occupational exposure to 1,3-benzenediamine may occur through inhalation and dermal contact with this compound at workplaces where 1,3-benzenediamine is produced or used(SRC). The general population may be exposed to 1,3-benzenediamine via dermal contact with consumer products containing this compound(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)

12 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 CAMEO Chemicals

16.5 UN GHS Classification

16.6 EPA CPDat Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 EPA DSSTox Classification

16.9 International Agency for Research on Cancer (IARC) Classification

16.10 Consumer Product Information Database Classification

16.11 EPA TSCA and CDR Classification

16.12 EPA Substance Registry Services Tree

16.13 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
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  12. Hazardous Substances Data Bank (HSDB)
  13. ILO-WHO International Chemical Safety Cards (ICSCs)
  14. New Zealand Environmental Protection Authority (EPA)
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  15. NJDOH RTK Hazardous Substance List
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    M-PHENYLENEDIAMINE (1,3-PHENYLENEDIAMINE)
    https://www.osha.gov/chemicaldata/84
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  26. EPA Regional Screening Levels for Chemical Contaminants at Superfund Sites
  27. Hazardous Chemical Information System (HCIS), Safe Work Australia
  28. NITE-CMC
    m-Phenylenediamine - FY2009 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/09-mhlw-2098e.html
    m-Phenylenediamine - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-0060e.html
    m-Phenylenediamine - FY2019 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/19-mhlw-2009e.html
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  30. IUPAC Digitized pKa Dataset
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  34. Japan Chemical Substance Dictionary (Nikkaji)
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  38. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
  39. SpectraBase
    m-PHENYLENDIAMINE (1,3-DIAMINOBENZENE)
    https://spectrabase.com/spectrum/7rM2b6xAQdf
  40. Metabolomics Workbench
  41. Nature Chemical Biology
  42. Nature Chemistry
  43. Springer Nature
  44. SpringerMaterials
  45. The Cambridge Structural Database
  46. Thieme Chemistry
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  54. EPA Substance Registry Services
  55. MolGenie
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    https://github.com/MolGenie/ontology/
  56. PATENTSCOPE (WIPO)
CONTENTS