95-83-0 Usage
Chemical Properties
4-Chloro-o-phenylenediamine is a brown crystalline powder or leaflets from water; freezing/melting point 67-73°C; also reported in lit. @ 76°C. Slightly soluble in water. soluble in benzene, very soluble in ethanol, ether.
Uses
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, but there is no evidence that it is currently used in the United States for these purposes (IARC 1982, HSDB 2009).
Production Methods
Commercial production of 4-chloro-o-PDA in the United
States was first reported in 1941. About 0.45–4.5 thousand kg
was produced by a U.S. company in 1977. It was also
produced by one company in the Federal Republic of
Germany. This compound has been patented as a hair dye
component, fur dyes, inks, and hair coloring formulations,
and is believed to be used to produce 5-chlorobenzotriazole,
an isomer of which is a photographic chemical.
The primary routes of potential human exposure to 4-
chloro-o-PDA are inhalation and dermal contact during its
production. Consumer exposure may occur from use of hair
dyes or products made from 5-chlorobenzotriazole.
Definition
ChEBI: 4-Chloro-ortho-phenylenediamine is a member of monochlorobenzenes. Undergoes cyclizations and cyclocondensations to form benzimidazoles.
General Description
4-chloro-o-phenylenediamine appears as brown crystalline solid or powder. (NTP, 1992)
Air & Water Reactions
4-Chloro-1,2-diaminobenzene may be sensitive to prolonged exposure to air and light. Insoluble in water.
Reactivity Profile
4-Chloro-1,2-diaminobenzene is incompatible with strong oxidizers. 4-Chloro-1,2-diaminobenzene reacts with alpha-ketoacids to form quinoxalones.
Fire Hazard
Flash point data for 4-Chloro-1,2-diaminobenzene are not available. 4-Chloro-1,2-diaminobenzene is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
neoplastigenic data. Human mutation data
reported. When heated to decomposition it
emits toxic fumes of Cland NOx. See also
AROMATIC AMINES.
Potential Exposure
This organochlorine material has been
patented as a hair dye component. It is believed to be used
in production of photographic chemicals. In varying
degrees, organochlorines are absorbed from the gut and
also by the lung and across the skin.
Carcinogenicity
4-Chloro-o-phenylenediamine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.
Purification Methods
Recrystallise the diamine from pet. ether. [Beilstein 13 IV 68.]
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Light sensitive. It reacts
with alpha-ketoacids to form quinoxalones or
benzopyrazines.
Check Digit Verification of cas no
The CAS Registry Mumber 95-83-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 95-83:
(4*9)+(3*5)+(2*8)+(1*3)=70
70 % 10 = 0
So 95-83-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H7ClN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2
95-83-0Relevant articles and documents
-
Maki,Hashimoto
, p. 602,603 (1954)
-
Efficient and recyclable bimetallic Co–Cu catalysts for selective hydrogenation of halogenated nitroarenes
Lu, Xionggang,Ren, Jiaan,Sheng, Yao,Wang, Xueguang,Wu, Baoqin,Zou, Xiujing
, (2021/12/20)
Silica supported N-doped carbon layers encapsulating Co–Cu nanoparticles (Co1Cux@CN/SiO2) were prepared by a one-step impregnation of Co(NO3)2·6H2O, Cu(NO3)2·3H2O, urea and glucose, following in situ carbothermal reduction. Effects of Cu contents on the catalytic performance of the Co1Cux@CN/SiO2 catalysts were investigated for selective hydrogenation of p-chloronitrobenzene to p-chloroaniline. The Co1Cu0.30@CN/SiO2 with Cu/Co molar ratio of 0.30:1 presented much higher activity and stability than the monometallic Co@CN/SiO2 catalyst. The addition of Cu into Co1Cux@CN/SiO2 catalysts had favorable effects on the formation of highly active Co–N sites and N-doped carbon layer. The role of the N-doped carbon layer was to protect the Co from oxidation by air, and the Co1Cu0.30@CN/SiO2 could be reused for at least 12 cycles without decrease in catalytic efficiency. Mechanistic and in situ infrared studies revealed that the interaction effect between the Co and Cu atoms made the surface of Co highly electron rich, which decreased adsorption of halogen groups and resulting in the enhanced selectivity during chemoselective hydrogenation of halogenated nitroarenes for a wide scope of substrates.
ARYL HYDROCARBON RECEPTOR ACTIVATORS
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Page/Page column 25-26, (2021/02/05)
Small molecule AhR ligands are disclosed. The ligands can induce the differentiation of Tr1 cells to suppress pathogenic immune responses without inducing nonspecific immune suppression. Methods of treatment of autoimmune diseases using the AhR ligands are also disclosed.
