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2-Amino-5-nitrophenol

PubChem CID
4984721
Structure
2-Amino-5-nitrophenol_small.png
2-Amino-5-nitrophenol_3D_Structure.png
Molecular Formula
Synonyms
  • 2-AMINO-5-NITROPHENOL
  • 121-88-0
  • 2-Hydroxy-4-nitroaniline
  • 5-Nitro-2-aminophenol
  • 3-Nitro-6-aminophenol
Molecular Weight
154.12 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
2-amino-5-nitrophenol appears as brown amorphous granules or powder. Melting point 198-202 °C.
2-Amino-5-nitrophenol is a member of 3-nitrophenols.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-Amino-5-nitrophenol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-5-nitrophenol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H6N2O3/c7-5-2-1-4(8(10)11)3-6(5)9/h1-3,9H,7H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC(=C(C=C1[N+](=O)[O-])O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H6N2O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

121-88-0

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Nikkaji Number

2.3.10 NSC Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-amino-5-nitrophenol
  • 2-hydroxy-4-nitroaniline
  • 3-hydroxy-4-aminonitrobenzene
  • 3-nitro-6-aminophenol
  • 5-nitro-2-aminophenol
  • Rodol YBA
  • Ursol Yellow Brown A

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
154.12 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.5
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
4
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
154.03784206 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
154.03784206 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
92.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
156
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

2-amino-5-nitrophenol appears as brown amorphous granules or powder. Melting point 198-202 °C.
Olive-brown, brown, or orange solid; [HSDB] Green crystalline solid; [MSDSonline]

3.2.2 Color / Form

Olive-brown, brown to orange crystalline solid
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. V57: 177 (1993)
Orange needles when recrystallized from water
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V2: 424 (1978)

3.2.3 Melting Point

388 to 396 °F (decomposes) (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.
205.8 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-22

3.2.4 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.
Slightly soluble in water
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. V57: 177 (1993)
Soluble in ethanol, acetone, and benzene
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. V57: 177 (1993)
Soluble in deuterated DSMO
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. V4: 4000

3.2.5 Vapor Pressure

0.0000352 [mmHg]

3.3 Chemical Classes

Nitrogen Compounds -> Nitrophenols

3.3.1 Cosmetics

Cosmetic ingredients (2-Amino-5-Nitrophenol) -> CIR (Cosmetic Ingredient Review)

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
1H NMR: 10012 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Copyright
Copyright © 2009-2024 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
303585
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
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker AM-270
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 6
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NIST Number
233820
Library
Main library
Total Peaks
64
m/z Top Peak
154
m/z 2nd Highest
80
m/z 3rd Highest
53
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2 of 6
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NIST Number
75945
Library
Replicate library
Total Peaks
50
m/z Top Peak
154
m/z 2nd Highest
80
m/z 3rd Highest
124
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4.2.2 LC-MS

1 of 9
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Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
15
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
11.039 min
Precursor m/z
153.0306
Precursor Adduct
[M-H]-
Top 5 Peaks

153.0304 999

122.0246 161

123.0324 29

106.0297 6

68.014 1

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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).
2 of 9
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
11.039 min
Precursor m/z
153.0306
Precursor Adduct
[M-H]-
Top 5 Peaks

153.0305 999

122.0246 163

123.0324 34

106.0296 5

124.0164 2

Thumbnail
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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).

4.2.3 Other MS

Other MS
MASS: 7945 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)

4.3 UV Spectra

UV: 6008 (Sadtler Research Laboratories Spectral Collection)
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. V4: 4000

4.4 IR Spectra

IR Spectra
IR: 21402 (Sadtler Research Laboratories IR Grating Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
G. AMERY, GILLETTE DEVELOPMENT LABORATORIES, READING, ENGLAND
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
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
10129
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
A70607
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
10129
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

The principal rat liver microsomal metabolite of 4-nitroaniline was isolated by high pressure liquid chromatography and was characterized as 2-amino-5-nitrophenol (2-hydroxy-4-nitroaniline) by comparison of its mass, nuclear magnetic resonance, and ultraviolet spectra and HPLC retention time to the synthetic compound. ... Pretreatment of rats with phenobarbital and 3-methylcholanthrene increased the rate of conversion of 4-nitroaniline to 2-hydroxy-4-nitroaniline by 2-fold and 4-fold, respectively; the reaction required NADPH and was inhibited by heat treatment of microsomes, by argon and carbon monoxide:oxygen atmospheres and by the cytochrome P-450 inhibitor, 2-[(2,4-dichloro-6-phenyl)phenoxy]ethylamine. ...
Anderson MM et al; Drug Metab Dispos 12 (2): 179-85 (1984)

8 Use and Manufacturing

8.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: 2-Amino-5-Nitrophenol
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 in hair dyes and to make azo dyes; [HSDB]
Industrial Processes with risk of exposure
Dressing Hair [Category: Other]
2-Amino-5-nitrophenol is used as an intermediate in the manufacture of several azo dyes, including CI Solvent Red 8, which is used for coloring synthetic resins, lacquers, inks and wood stains. It is also used as a dye in semi-permanent hair coloring products to produce red and gold-blond shades. It is used to a limited extent in permanent hair coloring products.
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. V57: 177 (1993)

8.2 Methods of Manufacturing

NITRATION OF O-ACETAMIDOPHENOL OR 2-METHYLBENZOXAZOLE IN SULFURIC ACID FOLLOWED BY HYDROLYSIS OF THE SEPARATED ISOMERS WITH SODIUM HYDROXIDE
SRI
2-Amino-5-nitrophenol is produced from 2-aminophenol by reaction with acetic anhydride to form 2-methylbenzoxazole, which is nitrated and hydrolysed to form 2-amino-5-nitrophenol.
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. V57: 177 (1993)
2-Amino-5-nitrophenol is prepared from 3-nitro-4-hyroxybenzenesulfonamide using sodium hyposulfite and caustic or zinc and HCl as the reducing agents. It may also be obtained from 2-amino-1-phenol-4-sulfonic acid by treatment with carbon disulfide to give a substituted benzoxazole whose ring is opened to the desired sulfonamide. It may be prepared by the chlorosulfonation of 2-chloronitrobenzene followed by aminolysis and hydrolysis.
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V2: 424 (1978)
Production is by nitration of benzoxazolone and separation from the 2-amino-4-nitro-phenol isomer after treatment with hydrochloric acid.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V2: 524 (2003)

8.3 Formulations / Preparations

2-Amino-5-nitrophenol is available commercially with the following specifications: purity, 98% (min); ash, 0.05% (max); iron, 40 ppm (max); lead, 5 ppm (max); arsenic, 2 ppm (max).
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. V57: 177 (1993)

8.4 U.S. Production

(1977) NOT PRODUCED COMMERCIALLY IN US
SRI
(1979) NOT PRODUCED COMMERCIALLY IN US
SRI
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
10 thousand - 500 thousand
Year
1990
Production Range (pounds)
No Reports
Year
1994
Production Range (pounds)
No Reports
Year
1998
Production Range (pounds)
10 thousand - 500 thousand
Year
2002
Production Range (pounds)
No Reports
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Phenol, 2-amino-5-nitro- (121-88-0). Available from, as of October 31, 2007: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html

8.5 U.S. Imports

(1977) 2.33X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI
(1979) 5.95X10+6 GRAMS (PRINCPL CUSTMS DISTS)
SRI

8.6 General Manufacturing Information

EPA TSCA Commercial Activity Status
Phenol, 2-amino-5-nitro-: ACTIVE
2-Amino-5-nitrophenol is not produced in commercial quantities in the USA. It is available in research quantities, at purities ranging from 90-99% from Jos. H. Lowenstein & Sons, 1991; TCI America, 1991; Aldrich Chemical Co., 1992; Fluka Chemie AG, 1993.
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. V57: 177 (1993)

9 Identification

9.1 Analytic Laboratory Methods

Analyte: 2-amino-5-nitrophenol; matrix: chemical purity; procedure: thin-layer chromatography
DHHS/NTP; Toxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice Technical Report Series No. 334 (1988) NIH Publication No. 88-2590
Analyte: 2-amino-5-nitrophenol; matrix: chemical purity, stability; procedure: high-performance liquid chromatography with ultraviolet detection at 254 nm
DHHS/NTP; Toxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice Technical Report Series No. 334 (1988) NIH Publication No. 88-2590

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
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Pictogram(s)
Irritant
Health Hazard
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H315 (94.4%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (> 99.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (94.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H351 (92.2%): Suspected of causing cancer [Warning Carcinogenicity]

H411 (97.6%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, 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 2188 reports by companies from 14 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

Skin Irrit. 2 (94.4%)

Eye Irrit. 2A (> 99.9%)

STOT SE 3 (94.3%)

Carc. 2 (92.2%)

Aquatic Chronic 2 (97.6%)

Skin sensitisation - category 1

10.1.3 Health Hazards

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract.

ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (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

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.

10.1.5 Hazards Summary

A mutagen and tumorigen; [RTECS] Causes diarrhea in high-dose feeding studies of rats; [HSDB] A skin, eye, mucous membrane, and upper respiratory tract irritant; [CAMEO] An irritant; [MSDSonline]

10.2 First Aid Measures

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure 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.

OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (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

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (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 Accidental Release Measures

10.4.1 Isolation and Evacuation

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

10.5 Handling and Storage

10.5.1 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 protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under 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 Exposure Control and Personal Protection

10.6.1 Personal Protective Equipment (PPE)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

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.

10.7 Stability and Reactivity

10.7.1 Air and Water Reactions

Is slowly oxidized by air at room temperature. Insoluble in water.

10.7.2 Reactive Group

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Phenols and Cresols

Amines, Aromatic

10.7.3 Reactivity Profile

2-AMINO-5-NITROPHENOL is a mild reducing agent. Incompatible with strong oxidizing agents. Reacts slowly with oxygen in the air at room temperature. Stable at temperatures up to 140 °F for two weeks when kept in the dark and under nitrogen. Stable under nitrogen for up to 24 weeks 77 °F. Incompatible with strong bases (NTP, 1992). Incompatible with acid chlorides and acid anhydrides.
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 Label

Poison

10.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Phenol, 2-amino-5-nitro-
REACH Registered Substance

10.10 Other Safety Information

Chemical Assessment
IMAP assessments - Phenol, 2-amino-5-nitro-: Human health tier II assessment

10.10.1 Special Reports

DHHS/NTP; Toxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 334 (1988) NIH Publication No. 88-2590

11 Toxicity

11.1 Toxicological Information

11.1.1 Evidence for Carcinogenicity

Evaluation: There is inadequate evidence in humans for the carcinogenicity of 2-amino-5-nitrophenol. There is limited evidence in experimental animals for the carcinogenicity of 2-amino-5-nitrophenol. Overall evaluation: 2-Amino-5-nitrophenol is not classifiable as to its carcinogenicity to humans (Group 3).
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. V57 183 (1993)

11.1.2 Carcinogen Classification

1 of 2
IARC Carcinogenic Agent
2-Amino-5-nitrophenol
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs
Volume 57: (1993) Occupational Exposures of Hairdressers and Barbers and Personal Use of Hair Colourants; Some Hair Dyes, Cosmetic Colourants, Industrial Dyestuffs and Aromatic Amines
2 of 2
NTP Technical Report
TR-334: Toxicology and Carcinogenesis Studies of 2-Amino-5-Nitrophenol (CASRN 121-88-0) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (1988 )
Peer Review Date
Conclusion for Male Rat
Some Evidence Some Evidence
Conclusion for Female Rat
No Evidence No Evidence
Conclusion for Male Mice
No Evidence No Evidence
Conclusion for Female Mice
No Evidence No Evidence
Summary
Under the conditions of these 2-year gavage studies, there was some evidence of carcinogenic activity for male F344/N rats that received 100 mg/kg 2-amino-5-nitrophenol, as shown by the increased incidence of acinar cell adenomas of the pancreas. Reduced survival of male F344/N rats that received 200 mg/kg decreased the sensitivity of this group for detecting a carcinogenic response. There was no evidence of carcinogenic activity for female rats that received 100 or 200 mg/kg per day. Marginally increased incidences of preputial or clitoral gland adenomas or carcinomas (combined) occurred in male and female F344/N rats administered 200 mg/kg 2-amino-5-nitrophenol. There was no evidence of carcinogenic activity for B6C3F1 mice that received 400 mg/kg 2-amino-5-nitrophenol; reduced survival of B6C3F1 mice that received 800 mg/kg caused this group to be considered inadequate for detecting a carcinogenic response.

11.1.3 Acute Effects

11.1.4 Medical Surveillance

Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.
ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute, 1988., p. 367

11.1.5 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Male Charles River CD rats (10 per group) received intraperitoneally either 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, or 4-amino-2-nitrophenol in a 10% aqueous DMSO solution. The LD50 for 2-amino-4-nitrophenol was reported to be 246 mg/kg, the LD50 for 2-amino-5-nitrophenol was reported to be greater than 800 mg/kg, and the LD50 for 4-amino-2-nitrophenol was reported to be 302 mg/kg.
Cosmetic Ingredient Review; Final Report of the Cosmetic Review Panel; Safety Assessment of 2-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol, 2-Amino-5-Nitrophenol, 4-Amino-2-Nitrophenol, 4-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol Sulfate, 3-Nitro-p-Hydroxyethylaminophenol, 4-Hydroxypropylamino-3-Nitrophenol. August 15, 2006.
/LABORATORY ANIMALS: Acute Exposure/ 2-Amino-4-nitrophenol, 2-amino-5-nitrophenol, and 4-amino-2-nitrophenol were orally administered to groups of five Charles River CD rats of each sex in an oil-in-water emulsion. The LD50 values for 2-amino-4-nitrophenol and 2-amino-5-nitrophenol were greater than 4000 mg/kg and the LD50 for 4-amino-2-nitrophenol was calculated to be 33 mg/kg.
Cosmetic Ingredient Review; Final Report of the Cosmetic Review Panel; Safety Assessment of 2-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol, 2-Amino-5-Nitrophenol, 4-Amino-2-Nitrophenol, 4-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol Sulfate, 3-Nitro-p-Hydroxyethylaminophenol, 4-Hydroxypropylamino-3-Nitrophenol. August 15, 2006.
/LABORATORY ANIMALS: Acute Exposure/ ... This study tested 33 dyes in guinea pigs using a modified Buehler and Klecak method for open epicutaneous testing. The dyes were tested at an induction concentration of 10% and challenge concentrations of 10.0%, 5.0%, and 2.5%. Nine of the 33 dyes tested /including 2-amino-5-nitrophenol/ produced positive allergic reactions in the guinea pig model ... . When eight of the nine positive dyes were retested using a 1% induction concentration, five dyes /including 2-amino-5-nitrophenol/ produced allergic contact dermatitis at a 1% challenge concentration ... , two at a 0.5% challenge concentration ( /including/ 2-amino-5-nitrophenol ... ), and one at a 0.25% challenge concentration (2-amino-5-nitrophenol). DNCB at a 0.5% induction/challenge concentration was used as a positive control. ...
Dinardo J, Draelos ZD; J Cosmet Sci 58 (3): 209-14 (2007)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Sixty B6C3F-1 mice were divided into six groups containing five mice/sex/group. The mice received either twelve doses of 2-amino-5-nitrophenol or corn oil (control material) at one of the following doses: 0, 313, 625, 1250, 2500, or 5000 mg/kg over a 16-day period. Clinical observations were performed twice daily, body weights were recorded weekly, and animals were necropsied. Nineteen mice died prior to the end of the study. Two males and five females died in the 5000 mg/kg group, three males and three females died in the 2500 mg/kg group, one female died in the 625 mg/kg group and two vehicle control males died. No significant difference in body weights occurred between treated and control animals and clinical observations were limited to loose stools in the males in the 5000 mg/kg group and two males were prostrate for the first week of the study in the 2500 mg/kg group. The LD50 in mice was greater than 1250 mg/kg but less than 2500 mg/kg.
Cosmetic Ingredient Review; Final Report of the Cosmetic Review Panel; Safety Assessment of 2-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol, 2-Amino-5-Nitrophenol, 4-Amino-2-Nitrophenol, 4-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol Sulfate, 3-Nitro-p-Hydroxyethylaminophenol, 4-Hydroxypropylamino-3-Nitrophenol. August 15, 2006.
For more Non-Human Toxicity Excerpts (Complete) data for 2-AMINO-5-NITROPHENOL (14 total), please visit the HSDB record page.

11.1.6 Non-Human Toxicity Values

The LD50 of 2-amino-5-nitrophenol in rats has been reported to be greater than 4000 mg/kg bw by oral administration and greater than 800 mg/kg bw by ip injection ... .
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. V57 180 (1993)
LD50 Mouse oral >1250 mg/kg to < 2500 mg/kg
Cosmetic Ingredient Review; Final Report of the Cosmetic Review Panel; Safety Assessment of 2-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol, 2-Amino-5-Nitrophenol, 4-Amino-2-Nitrophenol, 4-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol Sulfate, 3-Nitro-p-Hydroxyethylaminophenol, 4-Hydroxypropylamino-3-Nitrophenol. August 15, 2006.
LD50 Rat oral >2500 mg/kg
Cosmetic Ingredient Review; Final Report of the Cosmetic Review Panel; Safety Assessment of 2-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol, 2-Amino-5-Nitrophenol, 4-Amino-2-Nitrophenol, 4-Amino-3-Nitrophenol, 2-Amino-4-Nitrophenol Sulfate, 3-Nitro-p-Hydroxyethylaminophenol, 4-Hydroxypropylamino-3-Nitrophenol. August 15, 2006.

11.1.7 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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=121-88-0]

11.1.8 National Toxicology Program Studies

Sixteen-Day and Thirteen-Week Studies: During the 16-day studies, F344/N rats of each sex received 0, 156, 313, 625, 1,250, or 2,500 mg/kg 2-amino-5-nitrophenol by gavage in corn oil vehicle. One of the five males that received 2,500 mg/kg, 1/5 females that received 1,250 mg/kg, and 2/5 females that received 313 mg/kg died before the end of the studies. Final mean body weights of rats that received 1,250 or 2,500 mg/kg were 11% and 30% lower than that of vehicle controls for males and 9% and 13% lower for females. B6C3F1 mice of each sex received doses of 0, 313, 625, 1,250, 2,500, or 5,000 mg/kg 2-amino-5-nitrophenol. Two of five males and 5/5 females that received 5,000 mg/kg, 3/5 males and 3/5 females that received 2,500 mg/kg, 3/5 females that received 1,250 mg/kg, 1/5 females that received 625 mg/kg, and 2/5 male vehicle controls died before the end of the studies. Final mean body weights of chemically exposed mice were not different from those of the vehicle controls. Rats that received 625, 1,250, or 2,500 mg/kg and male mice that received 5,000 mg/kg had loose stools. In 13-week studies, F344/N rats and B6C3F1 mice of both sexes received 0, 100, 200, 400, 800, or 1,600 mg/kg 2-amino-5-nitrophenol by gavage in corn oil. Five of 10 male and 2/10 female rats that received 1,600 mg/kg, 1/10 male and 3/10 female rats that received 800 mg/kg, and 1/10 male rats that received 400 mg/kg died before the end of the studies. Final mean body weights of males that received 400, 800, or 1,600 mg/kg were 10%, 25%, and 43% lower than that of vehicle controls. The final mean body weight of females that received 1,600 mg/kg was 16% lower that of vehicle controls. Four of 10 male and 3/10 female mice that received 1,600 mg/kg died before the end of the 13-week studies. The final mean body weight of male mice that received 1,600 mg/kg was 11% lower than that of vehicle controls; male and female mice that received 1,600 mg/kg appeared lethargic. During the 13-week studies, acute/chronic perivasculitis of vessels of the cecum and colon was observed in rats that received 400, 800, or 1,600 mg/kg and in mice that received 1,600 mg/kg.
DHHS/NTP; Toxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice Technical Report Series No. 334 (1988) NIH Publication No. 88-2590
Body Weight and Survival in the Two-Year Studies: Mean body weights of rats receiving 200 mg/kg were 5%-10% lower than those of vehicle controls after week 33 for males and 4%-5% lower than those of vehicle controls after week 93 for females. Survival of male rats was significantly lower than that of vehicle controls after week 99 for the 100 mg/kg dose group and after week 75 for the 200 mg/kg dose group (final survival: vehicle control, 33/50; 100 mg/kg group, 16/50; 200 mg/kg group, 4/50). Survival of female rats was comparable to that of vehicle controls (30/50; 32/50; 29/50). Loose or poorly formed stools were observed for male rats and occasionally for females that received 200 mg/kg. Mean body weights of mice that received 800 mg/kg were 8%-11% lower than those of vehicle controls between weeks 29 and 74 for males and 8%-13% lower than those of vehicle controls after week 69 for females; mean body weights of mice that received 400 mg/kg were greater than those of vehicle controls after week 69 for males and 5%-9% lower than those of vehicle controls after week 69 for females. Survival of mice that received 800 mg/kg was significantly reduced compared with that of vehicle controls after week 20 for males and week 22 for females and was not considered adequate to evaluate a carcinogenic response (final survival--male: vehicle control, 31/50; 400 mg/kg group, 36/50; 800 mg/kg group, 12/50; female: 37/50; 36/50; 10/50). Nonneoplastic and Neoplastic Effects in the Two-Year Studies: Pigmentation was present at increased incidences in all groups of chemically exposed animals and was characterized by varying amounts of an orange, granular pigment present in the fibrous connective tissue of the lamina propria, in the submucosa, and around vessels in the submucosa of the cecum and colon. Pigmentation of the rectum was observed at increased incidences in male rats that received 100 mg/kg, male and female rats that received 200 mg/kg, and both groups of chemically exposed mice. No pigmentation was found in the intestines of vehicle control rats or mice. Associated with pigmentation was an increased incidence of acute/chronic inflammation in the cecum and colon of all groups chemically exposed rats and mice; this inflammation was similar to that observed in the 13-week studies but was of greater severity. Acute/chronic inflammation was also present in the rectum of male rats that received 100 mg/kg, male and female rats that received 200 mg/kg, and male mice that received 800 mg/kg. The incidence of pancreatic acinar cell adenomas was significantly increased (P<0.002) in male rats that received 100 mg/kg 2-amino-5-nitrophenol (vehicle control, 1/50; 100 mg/kg, 10/50; 200 mg/kg, 3/49); the increase was considered to be associated with chemical exposure. The reduced survival of male rats that received 200 mg/kg markedly reduced the sensitivity of this group for detecting the presence of neoplasms. The incidences of adenomas or carcinomas (combined) of the preputial or clitoral glands were marginally increased in male or female rats that received 200 mg/kg 2-amino-5-nitrophenol (preputial gland: 3/50; 2/50; 5/50; clitoral gland: 3/50; 3/50; 7/50). Neoplasms found in the intestinal tract of 3/50 male rats that received 100 mg/kg (one leiomyoma of the small intestine, one adenocarcinoma of the jejunum, one leiomyoma of the cecum), 2/50 male rats that received 200 mg/kg (one lipoma and one osteosarcoma of the cecum), and 1/50 female rats that received 200 mg/kg (one leiomyoma of the cecum) were not considered to be the result of chemical exposure. No compound-related neoplasms were found in mice exposed to 2-amino-5-nitrophenol in the 2-year studies.
DHHS/NTP; Toxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice Technical Report Series No. 334 (1988) NIH Publication No. 88-2590

11.1.9 Populations at Special Risk

Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.
ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute, 1988., p. 367

11.2 Ecological Information

11.2.1 Environmental Fate / Exposure Summary

2-Amino-5-nitrophenol's production and use as an intermediate in the manufacture of azo dyes and its use as a dye in semi-permanent hair coloring products and limited use in permanent hair coloring products may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 3.5X10-5 mm Hg at 25 °C indicates 2-amino-5-nitrophenol will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase 2-amino-5-nitrophenol 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 41 hours. Particulate-phase 2-amino-5-nitrophenol will be removed from the atmosphere by wet or dry deposition. 2-Amino-5-nitrophenol contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 2-amino-5-nitrophenol is expected to have high mobility based upon an estimated Koc of 85. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole. Biodegradation data were not available. If released into water, 2-amino-5-nitrophenol is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for 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. Occupational exposure to 2-amino-5-nitrophenol may occur through dermal contact with this compound at workplaces where 2-amino-5-nitrophenol is produced or used. Use data indicates that the general population may be exposed to 2-amino-5-nitrophenol via dermal contact with consumer products containing 2-amino-5-nitrophenol. (SRC)

11.2.2 Artificial Pollution Sources

2-Amino-5-nitrophenol's production and use as an intermediate in the manufacture azo dyes, which are used for coloring synthetic resins, lacquers, inks and wood stains and its use as a dye in semi-permanent hair coloring products and limited use in permanent hair coloring products(1) may result in its release to the environment through various waste streams.
(1) IARC; Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organizaiton, International Agency for Research on Cancer, 1972-Present 57: 177 (1993)

11.2.3 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrophenol is expected to have high mobility in soil(SRC). Volatilization of 2-amino-5-nitrophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Amino-5-nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2007).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.99(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2007).
(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. 4-9, 7-4, 7-5, 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-amino-5-nitrophenol, which has an estimated vapor pressure of 3.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-amino-5-nitrophenol 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 41 hours(SRC), calculated from its rate constant of 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-amino-5-nitrophenol may be removed from the air by wet or dry deposition(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

11.2.4 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of 2-amino-5-nitrophenol with photochemically-produced hydroxyl radicals has been estimated as 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 41 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Amino-5-nitrophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Amino-5-nitrophenol contains chromophores that absorb at wavelengths >290 nm(3) and therefore may 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, 8-12 (1990)

11.2.5 Environmental Bioconcentration

An estimated BCF of 3 was calculated in fish for 2-amino-5-nitrophenol(SRC), using an estimated log Kow of 0.99(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) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.6 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-amino-5-nitrophenol can be estimated to be 85(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-amino-5-nitrophenol is expected to have high mobility in soil(SRC).
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)

11.2.7 Volatilization from Water / Soil

The Henry's Law constant for 2-amino-5-nitrophenol is estimated as 7.8X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-amino-5-nitrophenol is expected to be essentially nonvolatile from water surfaces(2). 2-Amino-5-nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

11.2.8 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 14,512 workers (11,827 of these are female) are potentially exposed to 2-amino-5-nitrophenol in the US(1). Occupational exposure to 2-amino-5-nitrophenol may occur through dermal contact with this compound at workplaces where 2-amino-5-nitrophenol is produced or used(SRC). Use data indicates that the general population may be exposed to 2-amino-5-nitrophenol via dermal contact with consumer products containing 2-amino-5-nitrophenol(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 at https://www.cdc.gov/noes/ as of Nov 2007.

12 Associated Disorders and Diseases

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 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 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 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 CAMEO Chemicals

17.5 UN GHS Classification

17.6 EPA CPDat Classification

17.7 NORMAN Suspect List Exchange Classification

17.8 EPA DSSTox Classification

17.9 International Agency for Research on Cancer (IARC) Classification

17.10 EPA TSCA and CDR Classification

17.11 EPA Substance Registry Services Tree

17.12 MolGenie Organic Chemistry Ontology

18 Information Sources

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  8. European Chemicals Agency (ECHA)
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    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  9. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Hazardous Substances Data Bank (HSDB)
  11. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
    2-Amino-5-nitrophenol
    https://haz-map.com/Agents/3061
  12. ChEBI
  13. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  14. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  15. Cosmetic Ingredient Review (CIR)
  16. EPA Chemical and Products Database (CPDat)
  17. Hazardous Chemical Information System (HCIS), Safe Work Australia
  18. NMRShiftDB
  19. International Agency for Research on Cancer (IARC)
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    https://publications.iarc.fr/Terms-Of-Use
    IARC Classification
    https://www.iarc.fr/
  20. NTP Technical Reports
  21. Japan Chemical Substance Dictionary (Nikkaji)
  22. KEGG
    LICENSE
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    https://www.kegg.jp/kegg/legal.html
  23. MassBank Europe
  24. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  25. NIST Mass Spectrometry Data Center
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    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Phenol, 2-amino-5-nitro-
    http://www.nist.gov/srd/nist1a.cfm
  26. SpectraBase
  27. Springer Nature
  28. Thieme Chemistry
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
  29. Wikidata
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  32. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  33. GHS Classification (UNECE)
  34. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  35. EPA Substance Registry Services
  36. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  37. PATENTSCOPE (WIPO)
CONTENTS