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o-PHENYLENEDIAMINE

PubChem CID
7243
Structure
o-PHENYLENEDIAMINE_small.png
o-PHENYLENEDIAMINE_3D_Structure.png
o-PHENYLENEDIAMINE__Crystal_Structure.png
Molecular Formula
Synonyms
  • O-PHENYLENEDIAMINE
  • benzene-1,2-diamine
  • 95-54-5
  • 1,2-Phenylenediamine
  • 1,2-Diaminobenzene
Molecular Weight
108.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
o-Phenylenediamine and its salts can cause cancer according to The Environmental Protection Agency (EPA).
1,2-phenylenediamine appears as colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.
1,2-phenylenediamine is a phenylenediamine in which the two amino groups are ortho to each other. It has a role as a hydrogen donor. It derives from a hydride of a benzene.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
o-PHENYLENEDIAMINE.png

1.2 3D Conformer

1.3 Crystal Structures

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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-1,2-diamine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC=C(C(=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

95-54-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 UN Number

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 ICSC Number

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,2-diaminobenzene
  • 1,2-diaminobenzene dihydrochloride
  • 1,2-phenylenediamine
  • 2,3-diaminobenzene
  • o-phenylenediamine
  • ortho-phenylenediamine
  • orthophenylenediamine

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
0.1
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
62.9
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

1,2-phenylenediamine appears as colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.
Other Solid
Colorless to brownish-yellow solid that darkens on exposure to light and air; [CHEMINFO]
BROWN-TO-YELLOW CRYSTALS. TURNS DARK ON EXPOSURE TO LIGHT.
Colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid.

3.2.2 Color / Form

Brownish-yellow leaflets from water; plates from chloroform
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-34
Tan crystals or leaflets from water
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. V3: 2910
White crystalline solid when pure
Smiley R; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Phenylene- and Toluenediamines. Online Posting Date: 15 Jun 2000

3.2.3 Boiling Point

493 to 496 °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.
257 °C
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-34
256-258 °C
493-496 °F

3.2.4 Melting Point

216 to 219 °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.
219 °F
102.1 °C
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-34
103-104 °C
216-219 °F

3.2.5 Flash Point

313 °F (NFPA, 2010)
National Fire Protection Association. 2010. Fire Protection Guide to Hazardous Materials, 14th edition, edited by Guy R. Colonna. Quincy, MA: National Fire Protection Association. Note that this information is subject to the copyright restrictions of the organization that provided the data.
313 °F; 156 °C (Closed cup)
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-98
156 °C c.c.
313 °F

3.2.6 Solubility

less than 1 mg/mL at 68 °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.
Because of ... limited solubility in cold water/o-phenylenediamine/ can be recrystalized from water
Smiley R; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Phenylene- and Toluenediamines. Online Posting Date: 15 Jun 2000
Freely soluble in alcohol, chloroform, ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1257
Soluble in water, ethyl ether, benzene, chloroform; very soluble in ethanol
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-34
In water, 4.07X10+4 mg/L at 35 °C
Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 267
Solubility in water, g/100ml at 35 °C: 0.4

3.2.7 Vapor Density

Relative vapor density (air = 1): 3.73

3.2.8 Vapor Pressure

2.06X10-3 mm Hg at 25 °C
Yaws CL; Handbook of Vapor Pressure. Vol 3: C8-C28 Compounds. Houston, TX: Gulf Pub Co (1994)
Vapor pressure, kPa at 20 °C: 0.0013

3.2.9 LogP

log Kow = 0.15
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 21
0.15 (calculated)

3.2.10 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. 2654

3.2.11 Dissociation Constants

pKa1 = less than 2; pKa2 = 4.47 at 25 °C
Dean, J.A. Handbook of Organic Chemistry. New York, NY: McGraw-Hill Book Co., 1987., p. 8-46

3.2.12 Collision Cross Section

129.1 Ų [M+H]+
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

Nitrogen Compounds -> Amines, Aromatic

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
MAX ABSORPTION (CYCLOHEXANE): 235.5 NM (LOG E= 3.82); 289 NM (LOG E= 3.54); SADTLER REFERENCE NUMBER: 1604 (IR, PRISM); 460 (UV); 112 (NMR)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
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
P23938
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
MCB Manufacturing Chemists, Norwood, Ohio
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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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.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 8
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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 78.46

81 37.25

107 22.93

53 13.76

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License
CC BY-NC-SA
2 of 8
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
JEOL JMS-D-300
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

108 99.99

80 30.72

107 19.22

54 10.77

77 10.13

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License
CC BY-NC-SA

4.2.2 MS-MS

NIST Number
1054296
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
109.076
Total Peaks
4
m/z Top Peak
92
m/z 2nd Highest
67
m/z 3rd Highest
81
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4.2.3 Other MS

1 of 3
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Other MS
MASS: 1424 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
2 of 3
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Authors
TAJIMA S, GUNMA COLLEGE OF TECHNOLOGY
Instrument
HITACHI RMU-7M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

108 999

80 785

81 373

107 229

53 138

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License
CC BY-NC-SA

4.3 UV Spectra

UV: 6-80 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 764

4.4 IR Spectra

IR Spectra
IR: 262 (Sadtler Research Laboratories IR Grating Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
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
Source of Sample
Merck-Schuchardt Hohenbrunn
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
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
P1805
Lot Number
TLVZH-LG
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
P23938
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
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
275786
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
P1805
Lot Number
TLVZH-LG
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

A homologous series of hair dyes was selected for percutaneous absorption studies with excised human skin. The permeability constants obtained for the dyes were compared with octanol/water and skin membrane/water partition coefficients. The compounds examined were: p-phenylenediamine, o-phenylenediamine, 2-nitro-p-phenylenediamine, 2-amino-4-nitrophenol, 4-chloro-m-phenylenediamine, and 4-amino-2-nitrophenol. Skin absorption of the dyes was observed when they were applied in an aqueous solution. With one exception, the octanol/water partition coefficients were in the same rank order as the permeability constants. The determination of the partitioning of the hair dyes between water and either stratum corneum or epidermis was more complex. Preliminary stratum corneum/water partition studies resulted in values that were in the reverse order of skin permeation. When binding of the compounds to components of the membrane was saturated, the partition values more closely duplicated the rank order of permeability of the dyes. Prediction of percutaneous absorption of substances based on their partition coefficients may be confounded if these compounds are capable of binding to skin.
Bronaugh RL, Congdon ER; J Invest Dermatol 83 (2): 124-27 (1984)

7.2 Metabolism / Metabolites

O-phenylenediamine yields o-acetamidoaniline in yeast; yields o-quinone probably in tea. /From table/
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. 23

7.3 Transformations

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used as a chemical intermediate, analytical reagent, and photographic developer; [CHEMINFO]
Industrial Processes with risk of exposure
Photographic Processing [Category: Other]
Hair-dye substance banned by the European Union (September 2007)
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. V99 516 (2010)
Manufacture of dyes, photographic developing agent, organic synthesis, laboratory reagent.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 975
Used for the preparation of benzimidazole-derived agricultural fungicides such as benomyl; other fungicide uses include thiophanate methyl (Topsin), a turf fungicide and fuberidazole; in the preparation of a variety of benzimidazoles used as veterinarian anthelmintics.
Smiley R; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Phenylene- and Toluenediamines. Online Posting Date: 15 Jun 2000
Fluorescent indicator, pH range 3.1-4.4, green fluorescence-nonfluorescence
Sabnis RW et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Indicator Reagents. Online Posting Date: 15 Apr 2009
For more Uses (Complete) data for O-PHENYLENEDIAMINE (6 total), please visit the HSDB record page.

8.1.1 Use Classification

Hazard Classes and Categories ->

8.2 Methods of Manufacturing

The principal route to o-phenylenediamine is by the reduction of 2-nitroaniline, which is produced by the amination of 2-chloronitrobenzene with ammonia. Hydrogenation can be achieved with a variety of reducing agents, such as iron powder, hydrazine, or hydrogen sulfide, but commercially it is performed catalytically in the liquid phase over a palladium catalyst.
Smiley RA; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Phenylene- and Toluenediamines. Online Posting Date: June 15, 2000
AMMONOLYSIS FOLLOWED BY REDUCTION OF O-CHLORONITROBENZENE; REDUCTION OF O-NITROANILINE WITH SODIUM SULFIDE IN AN AUTOCLAVE
SRI
Made by reducing o-nitroaniline with Zn and NaOH.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1257
Reduction of ortho-dinitrobenzene or nitroaniline with iron and hydrochloric acid. Method of purification: crystallization.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 975

8.3 Formulations / Preparations

Grades: Technical; 99.0% minimum purity.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 975

8.4 U.S. Production

Aggregated Product Volume

2019: 1,000,000 lb - <20,000,000 lb

2018: 1,000,000 lb - <20,000,000 lb

2017: 1,000,000 lb - <20,000,000 lb

2016: 1,000,000 lb - <20,000,000 lb

(1972) PROBABLY GREATER THAN 1.36X10+6 GRAMS
SRI
(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS
SRI
1,2-Benzenediamine is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. 1,2-Benzenediamine (95-54-5). Available from, as of November 6, 2012: https://www.epa.gov/hpv/pubs/general/opptsrch.htm
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
>1 million - 10 million
Year
1990
Production Range (pounds)
>1 million - 10 million
Year
1994
Production Range (pounds)
>1 million - 10 million
Year
1998
Production Range (pounds)
>1 million - 10 million
Year
2002
Production Range (pounds)
>1 million - 10 million
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). 1,2-Benzenediamine (95-54-5). Available from, as of November 6, 2012: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Benzenediamine. Aggregated National Production Volume: 1 to < 10 million pounds.
US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. 1,2-Benzenediamine (95-54-5). Available from, as of November 6, 2012: https://cfpub.epa.gov/iursearch/index.cfm?s=chem&err=t

8.5 U.S. Imports

(1974) 5.42X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI
(1975) 7.28X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI

8.6 General Manufacturing Information

EPA TSCA Commercial Activity Status
1,2-Benzenediamine: ACTIVE

9 Identification

9.1 Analytic Laboratory Methods

Method: OSHA 87; Procedure: high performance liquid chromatography using ultraviolet detector; Analyte: o-phenylenediamine; Matrix: air; Detection Limit: 2.1 ug/cu m.
U.S. Department of Labor/Occupational Safety and Health Administration's Index of Sampling and Analytical Methods. o-Phenylenediamine (95-54-5). Available from, as of November 7, 2012: https://www.osha.gov/dts/sltc/methods/toc.html
Identification and estimation of hair dye components by high-performance liquid phase chromatography.
MIDLER O, KARLESKIND A; PARFUMS, COSMENT, AROMAS, 23: 77-80, 83-5 (1978)
Method No. 87; m-, o- and p-Phenylenediamine, HPLC, quantitation limit 2.1 ug/cu-m (based on a 100-L air volume).
OSHA Analytical Methods Manual. 2nd ed., Part 1 Organic Substances, Vol IV Meth 81-102, Apr 1993. US Dept Labor Occupational Safety and Health, Admin, Direct Tech Supp, OSHA Technical Center, Salt Lake City, Utah

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 7
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Pictogram(s)
Acute Toxic
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

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

H312+H332 (47.6%): Harmful in contact with skin or if inhaled [Warning Acute toxicity, dermal; acute toxicity, inhalation]

H312 (99.8%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H317 (99.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (99.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (99.8%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H341 (99.6%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H351 (99.8%): Suspected of causing cancer [Warning Carcinogenicity]

H400 (99.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (99.8%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P333+P317, P337+P317, P362+P364, P391, 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 454 reports by companies from 18 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. 4 (99.8%)

Skin Sens. 1 (99.8%)

Eye Irrit. 2 (99.8%)

Acute Tox. 4 (99.8%)

Muta. 2 (99.6%)

Carc. 2 (99.8%)

Aquatic Acute 1 (99.3%)

Aquatic Chronic 1 (99.8%)

Carcinogenicity - category 2

Germ cell mutagenicity - category 2

Eye irritation - category 2A

Skin sensitisation - category 1

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 1

Acute toxicity (ingestion) - category 3

Acute toxicity (inhalation) - category 4

Acute toxicity (dermal) - category 4

10.1.3 NFPA Hazard Classification

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NFPA 704 Diamond
3-1-0
NFPA Health Rating
3 - Materials that, under emergency conditions, can cause serious or permanent injury.
NFPA Fire Rating
1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

10.1.4 Health Hazards

SYMPTOMS: Symptoms of exposure to this chemical may include skin and eye irritation, headache, drowsiness, mental confusion and liver damage.

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It is highly toxic by inhalation and skin absorption. (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.

10.1.5 Fire Hazards

Flash point data for this chemical are not available. It is probably combustible. (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. Finely dispersed particles form explosive mixtures in air.

10.1.6 Hazards Summary

At lethal concentrations, exposed animals have seizures and paralysis without anesthesia. [ChemIDplus] Methemoglobinemia is observed in acute animal studies. In subchronic studies, rats have anemia and elevated liver enzymes. Critical Effects are irritation; liver; blood; [ACGIH]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.

10.2 Safety and Hazard Properties

10.2.1 Flammable Limits

Lower flammable limit: 1.5%
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-98

10.2.2 Physical Dangers

Dust explosion possible if in powder or granular form, mixed with air.

10.2.3 Explosive Limits and Potential

Finely dispersed particles form explosive mixtures in air.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html
Explosive limits , vol% in air: 1.5-?

10.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap.
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. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

10.3.1 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.

10.4 Fire Fighting

Fires involving this material can be controlled with a dry chemical, car bon dioxide or Halon extinguisher. (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.
Use water spray, powder.

10.4.1 Fire Fighting Procedures

Use water spray, powder.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html

10.5 Accidental Release Measures

10.5.1 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)

10.5.2 Spillage Disposal

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. 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.

10.5.3 Cleanup Methods

Spillage Disposal. 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. Do not let this chemical enter the environment. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html

10.5.4 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Recommendable method: Incineration. (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

10.5.5 Preventive Measures

Do not eat, drink, or smoke during work. Wash hands before eating.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html

10.6 Handling and Storage

10.6.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, protect it from light, and store it at refrigerated temperatures. (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.

10.6.2 Safe Storage

Separated from food and feedstuffs. Well closed.

10.6.3 Storage Conditions

Separated from food and feedstuffs. Well closed.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html

10.7 Exposure Control and Personal Protection

10.7.1 Threshold Limit Values (TLV)

0.1 [mg/m3]
8 hr Time Weighted Avg (TWA): 0.1 mg/cu m.
American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. ACGIH, Cincinnati, OH 2012, p. 48
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.
American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. ACGIH, Cincinnati, OH 2012, p. 5
A3; Confirmed animal carcinogen with unknown relevance to humans.
American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. ACGIH, Cincinnati, OH 2012, p. 48
0.1 mg/m
TLV-TWA (Time Weighted Average)
0.1 mg/m³ [1988]

10.7.2 Occupational Exposure Limits (OEL)

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

10.7.3 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.

10.7.4 Effects of Short Term Exposure

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

10.7.5 Effects of Long Term Exposure

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in anaemia. This substance is possibly carcinogenic to humans.

10.7.6 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (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.
Closed system, ventilation, explosion-proof electrical equipment and lighting.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html
Use local exhaust or breathing protection.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html
Protective gloves. Protective clothing.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html
Wear safety goggles or eye protection in combination with breathing protection.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html

10.7.7 Preventions

Fire Prevention
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
Exposure Prevention
STRICT HYGIENE!
Inhalation Prevention
Use local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear safety goggles or eye protection in combination with breathing protection.
Ingestion Prevention
Do not eat, drink, or smoke during work. Wash hands before eating.

10.8 Stability and Reactivity

10.8.1 Air and Water Reactions

Soluble in water [Hawley]. Melting point 219 F. Flash point 277 F. Toxic by skin absorption, inhalation or ingestion. Even as a solid will spot downwind area brown/purple (Roger Patrick, DuPont Engineer).

10.8.2 Reactive Group

Amines, Aromatic

10.8.3 Reactivity Profile

1,2-PHENYLENEDIAMINE a weak aromatic amine base neutralizes acids in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Darkens on exposure to air (Roger Patrick, DuPont Engineer).

10.9 Transport Information

10.9.1 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. 2008 Emergency Response Guidebook. Washington, D.C. 2008
/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. 2008 Emergency Response Guidebook. Washington, D.C. 2008
/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. 2008 Emergency Response Guidebook. Washington, D.C. 2008
/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. 2008 Emergency Response Guidebook. Washington, D.C. 2008
For more DOT Emergency Guidelines (Complete) data for O-PHENYLENEDIAMINE (8 total), please visit the HSDB record page.

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

IMO 6.1; Phenylenediamines
UN 1673; Phenylenediamines

10.9.3 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)

10.9.4 DOT Label

Poison

10.9.5 Packaging and Labelling

Do not transport with food and feedstuffs.

10.9.6 EC Classification

Symbol: T, N; R: 20/21-25-36-40-43-50/53-68; S: (1/2)-28-36/37-45-60-61; Note: C

10.9.7 UN Classification

UN Hazard Class: 6.1; UN Pack Group: III

10.10 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1,2-Benzenediamine
California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Carcinogenicity

Authoritative List - IARC Carcinogens - 2B; Prop 65

Report - regardless of intended function of ingredient in the product

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
1,2-Phenylenediamine: HSNO Approval: HSR003048 Approved with controls

10.10.1 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. 1,2-Benzenediamine is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.
40 CFR 716.120 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 5, 2012: https://www.ecfr.gov
All persons who manufacture (including import or by-product manufacture) or process o -pda, or intend to manufacture or process ortho-phenylenediamine after the effective date of this rule to the end of the reimbursement period shall submit letters of intent to test, submit study plans, conduct tests, and submit data, or submit exemption applications as specified in paragraphs (c)(3), (d), and (e) of this section, subpart A of this part, and parts 790 and 792 of this chapter for single-phase rulemaking. Required testing: health efffects, chemical fate and environmental effects testing.
40 CFR 799.3300 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 5, 2012: https://www.ecfr.gov

10.11 Other Safety Information

Chemical Assessment

IMAP assessments - 1,2-Benzenediamine: Human health tier II assessment

Evaluation - Phenylenediamines

10.11.1 Toxic Combustion Products

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
International Program on Chemical Safety/Commission of the European Union; International Chemical Safety Card on o-Phenylenediamine (September 10, 2002). Available from, as of November 8, 2012: https://www.inchem.org/pages/icsc.html

10.11.2 Special Reports

TSCA CHIPs present a preliminary assessment of 1,2-Benzenediamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404.

11 Toxicity

11.1 Toxicological Information

11.1.1 EPA Provisional Peer-Reviewed Toxicity Values

Chemical Substance
Reference Dose (RfD), Chronic
4 x 10^-3 mg/kg-day
PPRTV Assessment
Weight-Of-Evidence (WOE)
Likely to be carcinogenic to humans
Last Revision
2016

11.1.2 RAIS Toxicity Values

Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.004
Oral Chronic Reference Dose Reference
PPRTV Current
Oral Slope Factor (CSFo)(mg/kg-day)^-1
0.12
Oral Slope Factor Reference
PPRTV Current

11.1.3 Evidence for Carcinogenicity

A3; Confirmed animal carcinogen with unknown relevance to humans.
American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. ACGIH, Cincinnati, OH 2012, p. 48

11.1.4 Carcinogen Classification

IARC Carcinogenic Agent
ortho-Phenylenediamine
IARC Carcinogenic Classes
Group 2B: Possibly carcinogenic to humans
IARC Monographs
Volume 123: (2020) Some Nitrobenzenes and Other Industrial Chemicals

11.1.5 Exposure Routes

The substance can be absorbed into the body by inhalation and by ingestion.

11.1.6 Symptoms

Inhalation Exposure
Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.
Skin Exposure
Redness.
Eye Exposure
Redness. Pain.
Ingestion Exposure
See Inhalation.

11.1.7 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

IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.

ACGIH Carcinogen - Confirmed Animal.

11.1.8 Acute Effects

11.1.9 Toxicity Data

LC50 (rat) = 1,873 mg/m3

11.1.10 Antidote and Emergency Treatment

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient 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 the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 194
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 194-5
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 195

11.1.11 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Produces severe local reactions and systemic effects from percutaneous absorption and from ingestion. Local actions include severe dermatitis and urticaria; in the eye, chemosis, lacrimation, exophthalmos, ophthalmia, and even permanent blindness. Systemic actions include asthma, gastritis (regardless of portal of entry), rise in blood pressure, transudation into serous cavities, vertigo, tremors, convulsions and coma. ... The ortho isomer (diolene) is less toxic than the para (orsin). Neither is believed to be capable of inducing significant methemoglobinemia.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-210
/GENOTOXICITY/ Chromosomal aberration tests that were performed ... in peripheral human lymphocytes were ... positive with metabolic activation.
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.2 CD-ROM Cincinnati, OH 45240-4148 2012.

11.1.12 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ The signs of acute poisoning from o-phenylenediamine in animals included a poor general condition, disturbances in respiration, tremor, convulsions, excess salivation, and increased excitability. At autopsy, yellowish livers with spots, pale spleens, and kidneys were observed.
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
/LABORATORY ANIMALS: Acute Exposure/ In rats, o-phenylenediamine caused irritation of the stomach after oral intubation or slight irritation of the nose after inhalation.
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
/LABORATORY ANIMALS: Acute Exposure/ A single intraperitoneal injection of 100 umol o-phenylenediamine (suspended in propylene glycol)/kg body weight (=10.814 mg/kg) to male rats induced 10.8% methemoglobin.
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
/LABORATORY ANIMALS: Acute Exposure/ In cats, methemoglobin formation was weak with nonlethal oral doses (25-50 mg/kg), but high circulating concentrations occurred with lethal oral doses (250-500 mg/kg).
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
For more Non-Human Toxicity Excerpts (Complete) data for O-PHENYLENEDIAMINE (21 total), please visit the HSDB record page.

11.1.13 Non-Human Toxicity Values

LD50 Rat oral 660-1284 mg/kg, females more sensitive than males.
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
LD50 Mouse oral 331-450 mg/kg
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
LD50 Guinea pig oral 360 mg/kg
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
LD50 Rat ip 516 mg/kg
American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. o-Phenylenediamine p.1 CD-ROM Cincinnati, OH 45240-4148 2012.
For more Non-Human Toxicity Values (Complete) data for O-PHENYLENEDIAMINE (13 total), please visit the HSDB record page.

11.1.14 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of November 6, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-54-5]

11.1.15 TSCA Test Submissions

1,2-Benzenediamine (CAS # 95-54-5) was evaluated for eye irritation in 3 albino rabbits administered undiluted ocular instillations of 100 mg. The treated eyes remained unrinsed during post-instillation observation. Ocular irritation was maximal in all 3 rabbits 1 hour after treatment. A mean irritation score was 31.7/110. One rabbit remained unimproved at 72nd hour observation, developing corneal ulceration and vascularization by the 7th day, while Day 7 found complete resolution of all irritative signs in the other 2 treated rabbits. By 14th day observation period, one rabbit continued to show corneal vascularization and ulceration with slight conjunctival redness comprising an individual irritation score of 12/110 and a mean score (3 rabbits) of 4.0/110. Study investigators assigned a descriptive rating of "moderately irritating" to 1,2-benzenediamine.
CIBA-GEIGY CORP; Eye Irritation Test - Albino Rabbits; 2/6/75; EPA Doc No. 878213657; Fiche No. OTS0206431
o-Phenylenediamine (CAS # 95-54-5) was evaluated for oral neurotoxicity in Crl:CDBR rats (12/sex/group) administered single gavage doses of 0, 225, 450, and 900 mg/kg (10 mL/kg in methyl cellulose). 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. High-dose rats, 2 males and 4 females were found dead prior to scheduled sacrifice and significant weight loss within one day of dosing was common to all treatment groups, persisting throughout Day 4. Significant reductions in feed consumption were pronounced initially, but transient in all but the high-dose group. Clinical signs were most severe 2-4 days after treatment and included initial discolored urine, abnormal respiration with gasping, congestion, and sneezing (450, 900 mg/kg), dose-related malaise, postural changes, palpebral closure, and decreased arousal. The functional observational battery, fore-, and hindlimb grip strength and foot splay assessments were not indicative of a neurotoxicity at any treatment level. Motor activity was significantly depressed following treatment in all treatment groups relative to control. Study investigators attributed these findings to a general condition of dose-related malaise and reported no evidence of specific toxic effects on the central nervous system.
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
Acute dermal toxicity was evaluated in single New Zealand female rabbits receiving one occluded application of o-phenylenediamine to abraded skin at dose levels of 300, 1000, or 3000 mg/kg body weight for 24 hours. Mortality was not observed in any animal at any dose level, and the LD50 was reported to be greater than 3000 mg/kg. Clinical signs of toxicity were not observed, and the test article was not irritating to rabbit skin. Gross necropsy did not reveal any evidence of pathological effects.
INDUSTRIAL BIO-TEST LABORATORIES, INC; Acute Dermal Toxicity Study - Albino Rabbits (1975), EPA Document No. 878213658, Fiche No. OTS0206431
Acute inhalation toxicity was evaluated in 10 BR rats (5 male and 5 female) exposed to o-phenylene diamine vapor at a nominal concentration of 1340.0 mg/cu m for 4 hours. The atmosphere was generated by passing a stream of air through the test material in a gas wash bottle. Mortality was not observed in any animal during exposure or a 14 day observation period, and the LC50 was reported to be greater than 1340 mg/cu m. Clinical indications of toxicity were not observed, and necropsy of animals at 14 days did not reveal gross pathologic alterations.
INDUSTRIAL BIO-TEST LABORATORIES, INC; Acute Vapor Inhalation Toxicity Study with o-Phenylene Diamine Cake in Rats (1975), EPA Document No. 878213656, Fiche No. OTS0206431
For more TSCA Test Submissions (Complete) data for O-PHENYLENEDIAMINE (8 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 Ecotoxicity Values

LC50; Species: Brachydanio rerio (Zebrafish); Concentration: 24 mg/L for 96 hr /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 1782
LC100; Species: Brachydanio rerio (Zebrafish); Concentration: 33 mg/L for 96 hr /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 1782
LC50; Species: Pimephales promelas (Fathead minnow); Concentration: 44 mg/L for 96 hr /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 1782
LC50; Species: Pimephales promelas (Fathead minnow); Concentration: 271 mg/L for 96 hr /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 1782
For more Ecotoxicity Values (Complete) data for O-PHENYLENEDIAMINE (6 total), please visit the HSDB record page.

11.2.2 Ecotoxicity Excerpts

/AQUATIC SPECIES/ The static acute toxicities and degradative rates of the unsubstituted phenylenediamines (pdas) varied significantly among the ortho, para and meta isomers. With fathead minnows, the nominal 96 hr LC50s were 0.06, 44 and 1,600 mg/L for p-pda, o-pda and m-pda, respectively. In daphnid tests, the nominal 48 hr EC50s were 0.28, 0.87 and 5.9 mg/L for p-pda, o-pda and m-pda, respectively. The nominal 96 hr EC50s in algae were 0.28, 0.16, and 2.4 mg/L for p-pda, o-pda and m-pda, respectively. With oxygenation, the times to reach 1/2 initial concentrations were 4 to 9 hr for p-pda, 650 to 1,100 hr for o-pda and 3,200 to 8,100 hr for m-pda. Results suggest that acute toxicities of pdas are related to their chemical reactivities (degradative rates) and that pdas may degrade rapidly under environmental conditions.
Stahl RG Jr et al; Environ Toxicol Chem 9 (4): 485-8 (1990)
/OTHER TERRESTRIAL SPECIES/ ...The toxicity of 10 benzamines was tested by the well diffusion assay technique against 18 common bacterial species including the nitrogen-fixing bacterium Azotobacter vinelandii. ... o-Phenylenediamine was inhibitory to Escherichia coli, Klebsiella pnemoniae, Salmonella enteritidis, and Shigella sonnei. ... Because many of these organisms are common soil and aquatic bacteria, the accumulation of these benzamine compounds in the environment may have an adverse impact on soil biochemical activities.
Chung KT et al; Environ Toxicol Chem 16 (7): 1366-69 (1997)
/PLANTS/ Three isomers of the promutagen phenylenediamine at mM concentrations were plant-activated and induced mutation in stamen hairs of Tradescantia clone 4430. The rank order of the mutagenicity of the isomers was: o-phenylenediamine > m-phenylenediamine > p-phenylenediamine with corresponding mutagenic potencies of 5.60, 1.43, and 0.46 mutant stamen hair cells/mumole, respectively. Diethyldithiocarbamate (DEDTC) and ammonium meta-vanadate (vanadate) repressed the mutagenic activity of o-phenylenediamine (o-PDA) in intact plants. Based on inhibition kinetics and reaction rates, the mechanism of DEDTC antimutagenicity was attributed to the inhibition of peroxidases that are required in the plant activation of o-PDA to mutagenic product(s). Spectrophotometric measurements of equimolar concentrations of o-PDA and vanadate demonstrated that the antimutagenic property of vanadate was mainly due to its reactivity with o-PDA.
Gichner T, et al; Mutat Res 306 (2): 165-72 (1994)

11.2.3 US EPA Regional Screening Levels for Chemical Contaminants

1 of 2
Resident Soil (mg/kg)
5.50e+01
Industrial Soil (mg/kg)
8.20e+02
Tapwater (ug/L)
1.40e+01
MCL (ug/L)
1.5E+01(G)
Chronic Oral Reference Dose (mg/kg-day)
7.00e-04
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
2 of 2
Resident Soil (mg/kg)
1.00e+00
Industrial Soil (mg/kg)
1.90e+01
Tapwater (ug/L)
2.10e-01
MCL (ug/L)
1.5E+01(G)
Risk-based SSL (mg/kg)
5.6e-05
Oral Slope Factor (mg/kg-day)-1
1.20e-01
Chronic Oral Reference Dose (mg/kg-day)
4.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11.2.4 US EPA Regional Removal Management Levels for Chemical Contaminants

1 of 2
Resident Soil (mg/kg)
4.70e+01
Industrial Soil (mg/kg)
7.00e+02
Tapwater (ug/L)
7.90e+00
MCL (ug/L)
1.5E+01 (G)
Chronic Oral Reference Dose (mg/kg-day)
2.00e-04
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Soil Saturation Concentration (mg/kg)
1.29e+02
2 of 2
Resident Soil (mg/kg)
4.50e+02
Industrial Soil (mg/kg)
1.90e+03
Tapwater (ug/L)
6.50e+01
MCL (ug/L)
1.5E+01 (G)
Oral Slope Factor (mg/kg-day)-1
1.20e-01
Chronic Oral Reference Dose (mg/kg-day)
4.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11.2.5 ICSC Environmental Data

The substance is very toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment.

11.2.6 Environmental Fate / Exposure Summary

o-Phenylenediamine's production and use as a chemical intermediate in the manufacture of dyes; photographic developing agent; organic synthesis, and as a laboratory reagent may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 2.06X10-3 mm Hg at 25 °C indicates o-phenylenediamine will exist solely as a vapor in the atmosphere. Vapor-phase o-phenylenediamine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 0.7 hrs. o-Phenylenediamine absorbs light at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, o-phenylenediamine is expected to have very high mobility based upon an estimated Koc of 34. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group, suggesting that mobility may be much lower in some soils. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole. o-Phenylenediamine may not volatilize from dry soil surfaces based upon its vapor pressure. A 100% of total decomposition required greater than 64 days using a soil inoculum, suggesting that biodegradation is not an important environmental fate process in soil. If released into water, o-phenylenediamine is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. o-Phenylenediamine exhibited 33% removal after 5 days incubation using acclimated activated sludge inoculum, suggesting that biodegradation may be an important environmental fate process in water. Volatilization of the neutral species from water surfaces is not expected to be an important fate process for the neutral species based upon this compound's estimated Henry's Law constant. The pKa values of <2 and 4.47 indicate o-phenylenediamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 3 suggests bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to o-phenylenediamine may occur through inhalation and dermal contact with this compound at workplaces where o-phenylenediamine is produced or used. Use data indicate that the general population may be exposed to o-phenylenediamine via dermal contact with consumer products containing o-phenylenediamine. (SRC)

11.2.7 Artificial Pollution Sources

o-Phenylenediamine occurs as degradation product of thiophanate methyl & benomyl (benzimidazole fungicides).
Ishii Y et al; Noyaku Kensasho Hokoku 16: 30-8 (1976)
o-Phenylenediamine's production and use as a chemical intermediate in the manufacture of dyes, photographic developing agent, organic synthesis, and as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 15 th ed. New York, NY: John Wiley & Sons, Inc., p. 975 (2007)

11.2.8 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is expected to have very high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of o-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 2.06X10-3 mm Hg(5), and water solubility, 4.04X10+4 mg/L(6). o-Phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). A 100% of total decomposition required greater than 64 days using a soil inoculum(7), suggesting that biodegradation is not an important environmental fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Bollag JM et al; J Agric Food Chem 26: 1302-6 (1978)
(4) Adrian P et al; Toxicol Environ Chem 20-21: 109-20 (1989)
(5) Yaws CL; Handbook of Vapor Pressure. Vol 3: C8-C28 Compounds. Houston, TX: Gulf Pub Co (1994)
(6) Yalkowky SH et al; Handbook of Aqueous Solubility Data. 2nd ed. Boca Raton, FL: CRC Press, p. 267 (2010)
(7) Alexander M, Lustigman BK; J Agric Food Chem 14: 410-3 (1966)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.06X10-3 mm Hg(4), and water solubility, 4.04X10+4 mg/L(5). The pKa values of <2 and 4.47(6) indicate o-phenylenediamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC),from its log Kow of 0.15(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). o-Phenylenediamine exhibited 33% removal after 5 days incubation using acclimated activated sludge inoculum(10), suggesting that biodegradation may be an important environmental fate process in water(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Yaws CL; Handbook of Vapor Pressure. Vol 3: C8-C28 Compounds. Houston, TX: Gulf Pub Co (1994)
(5) Yalkowky SH et al; Handbook of Aqueous Solubility Data. 2nd ed. Boca Raton, FL: CRC Press, p. 267 (2010)
(6) Dean JA; Handbook of Organic Chemistry, New York, NY: McGraw-Hill, Inc p. 8-46 (1987)
(7) Franke C et al; Chemosphere 29: 1501-14 (1994)
(8) 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)
(9) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Nov 6, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(10) Pitter P; Water Res 10: 231-35 (1976)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phenylenediamine, which has a vapor pressure of 2.06X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phenylenediamine 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 0.7 hours(SRC), calculated from its rate constant of 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). o-Phenylenediamine absorbs light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Yaws CL; Handbook of Vapor Pressure. Vol 3: C8-C28 Compounds. Houston, TX: Gulf Pub Co (1994)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) NIST; NIST Chemistry WebBook. o-Phenylenediamine (95-54-5). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Nov 6, 2012: https://webbook.nist.gov

11.2.9 Environmental Biodegradation

AEROBIC: In an aerobic screening study using acclimated activated sludge inoculum, o-phenylenediamine (initial concentration of 25 to 30 ppm) exhibited 33% removal after 5 days incubation(1). In a screening test using soil microflora and an initial concentration of 10 ug/mL o-phenylenediamine, the decomposition period was observed to be >64 days for total loss of ultraviolet absorbency at a wavelength of 294 nm(2). o-Phenylenediamine (initial concentration of 500 ppm) exhibited a 44.5% theoretical BOD after 8 days in a Warburg respirometer using aniline-acclimated sludge at 20 °C(3). o-Phenylenediamine, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(4).
(1) Pitter P; Water Res 10: 231-35 (1976)
(2) Alexander M, Lustigman BK; J Agric Food Chem 14: 410-3 (1966)
(3) Malaney GW; J Water Pollut Control Fed 32: 1300-11 (1960)
(4) Sakuratani Y et al; SAR QSAR Environ Res 16: 403-31 (2005)

11.2.10 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of o-phenylenediamine with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). o-Phenylenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(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). o-Phenylenediamine absorbs light at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
(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) NIST; NIST Chemistry WebBook. o-Phenylenediamine (95-54-5). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Nov 6, 2012: https://webbook.nist.gov

11.2.11 Environmental Bioconcentration

An estimated BCF of 3 was calculated in fish for o-phenylenediamine(SRC), using a log Kow of 0.15(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for 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) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Nov 6, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.12 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of o-phenylenediamine can be estimated to be 34(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-phenylenediamine is expected to have very high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC).
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) Bollag JM et al; J Agric Food Chem 26: 1302-6 (1978)
(4) Adrian P et al; Toxicol Environ Chem 20-21: 109-20 (1989)

11.2.13 Volatilization from Water / Soil

The Henry's Law constant for o-phenylenediamine is estimated as 7.2X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.06X10-3 mm Hg(1), and water solubility, 4.04X10+4 mg/L(2). This Henry's Law constant indicates that the neutral species of o-phenylenediamine is expected to be essentially nonvolatile from water an dmoist soil surfaces(3). o-Phenylenediamine may exist partially in the ionized form at pH values of 5 to 9 based on pKa values of less than 2 and 4.47 at 25 °C(4). o-Phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) Yaws CL; Handbook of Vapor Pressure. Vol 3: C8-C28 Compounds. Houston, TX: Gulf Pub Co (1994)
(2) Yalkowky SH et al; Handbook of Aqueous Solubility Data. 2nd ed. Boca Raton, FL: CRC Press, p. 267 (2010)
(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, New York, NY: McGraw-Hill, Inc p. 8-46 (1987)

11.2.14 Probable Routes of Human Exposure

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of o-phenylenediamine is 1000 or greater; the data may be greatly underestimated(1).
(1) US EPA; Inventory Update Reporting (IUR). Non-confidential 2006 IUR Records by Chemical, including Manufacturing, Processing and Use Information. Washington, DC: U.S. Environmental Protection Agency. Available from, as of Oct 23, 2012: https://cfpub.epa.gov/iursearch/index.cfm
NIOSH (NOES Survey 1981-1983) has statistically estimated that 3,076 workers (1,372 of these were female) were potentially exposed to o-phenylenediamine in the US(1). Occupational exposure to o-phenylenediamine may occur through inhalation and dermal contact with this compound at workplaces where o-phenylenediamine is produced or used. Use data indicate that the general population may be exposed to o-phenylenediamine via dermal contact with consumer products containing o-phenylenediamine(SRC).
(1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available from, as of Nov 6, 2012: https://www.cdc.gov/noes/

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Nature Journal References

12.7 Chemical Co-Occurrences in Literature

12.8 Chemical-Gene Co-Occurrences in Literature

12.9 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

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 ChEMBL Target Tree

16.6 UN GHS 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 EPA TSCA and CDR Classification

16.11 EPA Substance Registry Services Tree

16.12 MolGenie Organic Chemistry Ontology

17 Information Sources

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  15. NJDOH RTK Hazardous Substance List
  16. Occupational Safety and Health Administration (OSHA)
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    https://rais.ornl.gov/
  18. California Safe Cosmetics Program (CSCP) Product Database
  19. California Office of Environmental Health Hazard Assessment (OEHHA)
  20. ChEBI
  21. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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  25. Crystallography Open Database (COD)
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  26. The Cambridge Structural Database
  27. EPA Regional Screening Levels for Chemical Contaminants at Superfund Sites
  28. Hazardous Chemical Information System (HCIS), Safe Work Australia
  29. NITE-CMC
    o-Phenylenediamine - FY2009 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/09-mhlw-2097e.html
    o-Phenylenediamine - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-0058e.html
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  31. IUPAC Digitized pKa Dataset
  32. NMRShiftDB
  33. MassBank Europe
  34. Human Metabolome Database (HMDB)
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  36. Japan Chemical Substance Dictionary (Nikkaji)
  37. KEGG
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  38. MassBank of North America (MoNA)
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  40. SpectraBase
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  41. Metabolomics Workbench
  42. Nature Chemical Biology
  43. NORMAN Suspect List Exchange
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  51. GHS Classification (UNECE)
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  53. MolGenie
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  54. PATENTSCOPE (WIPO)
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