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Details

Stereochemistry ACHIRAL
Molecular Formula C6H7ClN2
Molecular Weight 142.586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-CHLORO-O-PHENYLENEDIAMINE

SMILES

NC1=CC=C(Cl)C=C1N

InChI

InChIKey=BXIXXXYDDJVHDL-UHFFFAOYSA-N
InChI=1S/C6H7ClN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2

HIDE SMILES / InChI
Molecular Formula C6H7ClN2
Molecular Weight 142.586
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

4-Chloro-o-phenylenediamine is a chlorinated aromatic amine that exists as a brown crystalline solid or powder at room temperature. 4-Chloro-o-phenylenediamine can be used as an oxidation base for dye preparation, as a chemical intermediate to produce 5-chlorobenzotriazole, as a curing agent for epoxy resins, as a reagent in gas chromatography, and to synthesize experimental pharmaceuticals. It has been used as a chemical intermediate in dye production and was patented as a hair-dye component. Oral exposure to 4-chloro-o-phenylenediamine caused tumors in two rodent species and at several different tissue sites. Dietary administration of technical-grade 4-chloro-o-phenylenediamine caused benign or malignant liver tumors (hepatocellular adenoma or carcinoma) in mice of both sexes and benign or malignant tumors of the urinary bladder and forestomach (papilloma or carcinoma) in rats of both sexes (NCI 1978).

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study.
2015-05
Photodegradation of selected PCBs in the presence of Nano-TiO2 as catalyst and H2O2 as an oxidant.
2010-11
Use of cell viability assay data improves the prediction accuracy of conventional quantitative structure-activity relationship models of animal carcinogenicity.
2008-04
Single strand dna breaks in human lymphocytes exposed to para-phenylenediamine and its derivatives.
2008-01
Oxidative DNA damage induced by hair dye components ortho-phenylenediamines and the enhancement by superoxide dismutase.
2006-09-05
Evaluation of liver and peripheral blood micronucleus assays with 9 chemicals using young rats. A study by the Collaborative Study Group for the Micronucleus Test (CSGMT)/Japanese Environmental Mutagen Society (JEMS)-Mammalian Mutagenicity Study Group (MMS).
2005-06-06
4-Chloro-o-phenylenediamine.
2004
4-Chloro-o-phenylenediamine.
2002
Patents

Patents

05496590
1
06541486
1
07754713
2
08211901
2
08697685
8
08835648
1

Sample Use Guides

In Vivo Use Guide
In an initial 2-week study 4-C-o-PDA (4-Chloro-o-phenylenediamine) was administered daily per os to groups of male and female C57BL/6 Big Blue mice at doses of 0 and 200 mg/kg for 2 weeks (on working days) followed by a treatment free expression time of 10 days. Only a weak increase in the mutant frequencies in females was observed. In a 26-week study, where 4-C-o-PDA was given to groups of male and female Big Blue mice in feed at dietary concentrations of 0, 5,000 and 10,000 ppm, 4-C-o-PDA was found to induce a pronounced dose-dependent increase in mutant frequencies in either sex.
Route of Administration: Oral
In Vitro Use Guide
4-Chloro-o-phenylenediamine within the range of doses from 100 uM to 500 uM showed the genotoxicity in a dose-dependent manner after the incubation of lymphocytes for 2 h.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:23:24 GMT 2025
Edited
by admin
on Mon Mar 31 22:23:24 GMT 2025
Record UNII
8E72QRZ33H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-CHLORO-O-PHENYLENEDIAMINE
Common Name English
4-CHLORO-1,2-BENZENEDIAMINE
HSDB  
Preferred Name English
2-AMINO-4-CHLOROANILINE
Systematic Name English
5-CHLORO-1,2-PHENYLENEDIAMINE
Systematic Name English
4-CHLORO-1,2-BENZENEDIAMINE [HSDB]
Common Name English
4-CHLORO-ORTHO-PHENYLENEDIAMINE [IARC]
Common Name English
NSC-6157
Code English
3-CHLORO-1,6-PHENYLENEDIAMINE
Systematic Name English
1,2-DIAMINO-4-CHLOROBENZENE
Systematic Name English
1,2-BENZENEDIAMINE, 4-CHLORO-
Systematic Name English
3,4-DIAMINOCHLOROBENZENE
Systematic Name English
P-CHLORO-O-PHENYLENEDIAMINE
Common Name English
O-PHENYLENEDIAMINE, 4-CHLORO-
Systematic Name English
2-AMINO-5-CHLOROANILINE
Systematic Name English
3,4-DIAMINO-1-CHLOROBENZENE
Systematic Name English
URSOL OLIVE 6G
Brand Name English
4-CHLORO-1,2-PHENYLENEDIAMINE
Systematic Name English
CI 76015
Common Name English
2-AMINO-4-CHLOROBENZENAMINE
Systematic Name English
4-CHLORO-2-AMINOANILINE
Systematic Name English
4-CHLORO-1,2-DIAMINOBENZENE
Systematic Name English
Code System Code Type Description
FDA UNII
8E72QRZ33H
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-456-8
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID5020283
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
CAS
95-83-0
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
HSDB
5087
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
PUBCHEM
7263
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
NSC
6157
Created by admin on Mon Mar 31 22:23:24 GMT 2025 , Edited by admin on Mon Mar 31 22:23:24 GMT 2025
PRIMARY
NIH
NCATS
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