4-Aminodiphenylamine
Chemical compound
From Wikipedia, the free encyclopedia
4-Aminodiphenylamine is a diphenylamine with an additional amine substituent. This dimer of aniline has various industrial uses, including as a hair dye ingredient, but also has raised concerns about toxicity by skin contact.[1] It is also a starting material for the synthesis of 6PPD, an antiozonant for various rubber products.[2] A colorimetric test for the quantitative analysis of nitrite, at levels below 100 nanograms per milliliter, is based on nitrite-catalyzed coupling of 4-aminodiphenylamine with N,N-dimethylaniline.[3]
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| Names | |
|---|---|
| Preferred IUPAC name
N1-Phenylbenzene-1,4-diamine | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 908935 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.684 |
| EC Number |
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| 241334 | |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1673 |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H12N2 | |
| Molar mass | 184.242 g·mol−1 |
| Appearance | purple–black or dark purple |
| Density | 1.09 g/mL |
| Melting point | 75 °C (167 °F; 348 K) |
| Boiling point | 354 °C (669 °F; 627 K) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H317, H319, H410 | |
| P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
The most common route of industrial production is by the metal catalysed reaction of aniline with 4‑nitrochlorobenzene to give 4‑nitrodiphenylamine (Buchwald–Hartwig amination):
Subsequent hydrogenation gives 4-aminodiphenylamine.[4] An alternative is the direct reaction of nitrobenzene with aniline via a nucleophilic aromatic substitution of hydrogen (vicarious nucleophilic substitution).[5][6] This again requires a reduction step but is a good example of industrial green chemistry as it eliminates the need for organochlorine starting materials and metal catalysts.