Basic information
- CAS
615-66-7- Standard SMILES
Nc1ccc(N)c(Cl)c1- InChIKey
MGLZGLAFFOMWPB-UHFFFAOYSA-N- Molecular formula
- C6H7ClN2
- Average molar mass
- 142.58 g/mol
- Monoisotopic mass
- 142.0297759
Overview
2-chloro-1,4-phenylenediamine is a diamine that is 1,4-phenylenediamine substituted at position 2 by a chloro group. It has a role as a dye. It is a diamine and a member of monochlorobenzenes. It is functionally related to a 1,4-phenylenediamine. It is a conjugate base of a 2-chloro-1,4-phenylenediaminium.
Names & identifiers
- Preferred name
- 2-Chloro-p-Phenylenediamine
- IUPAC
- 2-chlorobenzene-1,4-diamine
- English name
- 2-Chloro-1,4-diaminobenzene
- Molecular formula
- C6H7ClN2
- Molecular weight
- 142.59
Names & synonyms
Show more names
Database identifiers
- CAS
615-66-7- PubChem CID
- 11998
- DTXSID
DTXSID3043944- ChEMBL
CHEMBL1619318- ChEBI
CHEBI:76598- UNII
- W949BCC82R
- EC Number
- 210-441-2
- Nikkaji
- J7.028I
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 52 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 97.1
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (2-Chloro-p-Phenylenediamine) -> CIR (Cosmetic Ingredient Review)
Hair dyeing
Physicochemical properties
- Melting point
- 62 · 62-66 °C
- Boiling point
- 232.49 °C · 232.49°C (rough estimate)
- Density
- 1.2124 · 1.2124 (rough estimate)
- vapor pressure
- 0.274 Pa · 0.274Pa at 25℃
- refractive index
- 1.521 · 1.5210 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- DMSO, Methanol (Slightly)
- form
- Solid
- pka
- 4.8 · 4.80±0.10(Predicted)
- color
- Very Dark Green to Black
- Water Solubility
- 49.61 g/L · 49.61g/L at 25℃
- λmax
- 318 nm · 318nm(EtOH)(lit.)
- Cosmetics Ingredients Functions
- HAIR DYEING
- Cosmetic Ingredient Review (CIR)
- 2 · 2-Chloro-1,4-diaminobenzene (615-66-7)
- LogP
- 0.44 at · 0.44 at 20℃
- CAS DataBase Reference
- 615 · 615-66-7(CAS DataBase Reference)
- FDA UNII
- 949 BCC82R · W949BCC82R
- EPA Substance Registry System
- 1 · 1,4-Benzenediamine, 2-chloro- (615-66-7)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 8925000 · SS8925000
- TSCA
- TSCA listed
- HS Code
- 2921.51 · 2921.51.5000
- Hazardous Substances Data
- 615 · 615-66-7(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
Chemical: 1,4-Benzenediamine, 2-chloro-
Status: Cease Manufacture Update: 30-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17518
1,4-Benzenediamine, 2-chloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Special Reports
Final Report on the safety assessment of 2-chloro-p-phenylenediamine and 2-chloro-p-phenylenediamine sulfate. J Am Coll Toxicol 11(4) 521-30 (1992).
Bioassay of 2-Chlorophenylenediamine Sulfate for Possible Carcinogenicity (1978) Technical Rpt Series No. 113 DHEW Pub No. (NIH) 78-1368, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity (ingestion) - category 4
Toxicology
Non-Human Toxicity Excerpts
2-CHLORO-P-PHENYLENEDIAMINE INCREASED TRANSITIONAL CELL HYPERPLASIA OF KIDNEY IN MALE & FEMALE RATS. IT HAD NO SIGNIFICANT NEOPLASTIC EFFECT AT THE 0.15 OR 0.3% LEVELS FED.
In an oral subchronic toxicity test using rats and mice, all male rats and one female rat died in the 1% concentration of 2-chloro-p-phenylenediamine dose group; at 0.3%, no rats or mice died but the mean body weight gain was depressed. In the mice, one of the males and none of the females died in the 1% dose group. In a test for ocular irritaion, 2.5% 2-chloro-p-phenylenediamine produced, at most, only mild conjunctival inflammation. ... not a sensitizer when assayed on abraded and intact skin.
National Toxicology Program Studies
A bioassay for possible carcinogenicity of 2-chloro-p-phenylenediamine sulfate was conducted using Fischer 344 rats and B6C3F1 mice. 2-Chloro-p-phenylenediamine sulfate was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. The dietary concentrations used in the chronic bioassay were 0.3 and 0.15% for the high and low dose rats, respectively, and 0.6 and 0.3% for the high and low dose mice, respectively. Compound administration was for 105 to 107 wk in rats, 87 wk in high dose mice, and 104-105 wk in low dose mice. The only groups observed during an untreated period after dosing were the high dose mice, observed for 18 wk after cmpd administration ceased. For each species, 20 animals of each sex were placed on test as controls. ... Under the conditions of this bioassay there was /no/ evidence that dietary administration of 2-chloro-p-phenylenediamine sulfate was carcinogenic to Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative. /2-Chlorophenylenediamine sulfate/
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SS8925000
- hs_code
- 2921.51.5000
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- Hazard statements
- H302-H315-H319-H332-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280-P305+P351+P338
- Hazardous Substances Data
- 615-66-7(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
CIR ingredient: 2-Chloro-p-Phenylenediamine
Used as a component of hair dyes; Not commercially produced in the US; [HSDB]
Dressing Hair [Category: Other]
INGREDIENT IN HAIR DYES
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1978) 1.0X10+6 G-PRINCPL CUSTMS DISTS-SULFATE
(1979) 8.0X10+5 G-PRINCPL CUSTMS DISTS-SULFATE
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Applications
UsesThis compound had some uses in hair dye formulations.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A diamine that is 1,4-phenylenediamine substituted at position 2 by a chloro group.
Related reactions
Compound notes
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