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| Names | |
|---|---|
| Preferred IUPAC name 3,3′-Dichloro[1,1′-biphenyl]-4,4′-diamine | |
| Other names 4-(4-Amino-3-chlorophenyl)-2-chloroaniline 4,4′-Diamino-3,3′-dichlorobiphenyl o,o'-Dichlorobenzidine 3,3′-Dichlorobiphenyl-4,4′-diamine 3,3′-Dichloro-4,4′-biphenyldiamine 3,3′-Dichloro-4,4′-diaminobiphenyl | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.001.918 |
| KEGG |
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| UNII | |
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| Properties | |
| C12H10Cl2N2 | |
| Molar mass | 253.13 g/mol |
| Appearance | Gray or purple crystalline solid |
| Melting point | 132 to 133 °C (270 to 271 °F; 405 to 406 K) |
| Boiling point | 402 °C (756 °F; 675 K) |
| 0.07% (15°C)[2] | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Potential carcinogen[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | carcinogen[2] |
REL (Recommended) | Ca[2] |
IDLH (Immediate danger) | Ca [N.D.][2] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
3,3'-Dichlorobenzidine is anorganic compound with the formula (C6H3Cl(NH2))2. The pure compound is pale yellow, but commercial samples are often colored. It is barely soluble in water and is often supplied as a wet paste. It is widely used in the production ofdiarylide yellow pigments used in the production of printing inks.[3] Its use in the production of dyes has been largely discontinued because of concerns about carcinogenicity.
3,3'-Dichlorobenzidine is prepared in two steps from2-nitrochlorobenzene. The first step involves reduction with zinc in base to afford 2,2'-dichlorodiphenylhydrazine. This intermediate undergoes thebenzidine rearrangement to afford 3,3'-dichlorobenzidine.[4]
Aqueous solutions of 3,3'-dichlorobenzidine degrade in light to monochloro derivative. It undergoes chlorination (for example in water treatment plants) to give the tetrachloro derivative.
The most widely practiced reaction of 3,3'-dichlorobenzidine is its doublediazotization. This bis(diazo) intermediate is then coupled to derivatives ofacetoacetylaminobenzene (CH3C(O)CH2C(O)NHAr). In this way, thediarylide commercial yellow pigments are produced:Pigment Yellow 12,Pigment Yellow 13,Pigment Yellow 14,Pigment Yellow 17,Pigment Orange 13,Pigment Yellow 81, andPigment Yellow 83.[3]
3,3'-Dichlorobenzidine is considered acarcinogen.[1] This compound has been shown to increase the incidence of tumors in animals.[6] Because it is structurally similar tobenzidine, a known carcinogen, it is believed that it may share a similar mechanism in causingbladder cancer in humans.[6]
