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4-Aminodiphenylamine

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. It is also a starting material for the synthesis of 6PPD, an antiozonant for various rubber products. 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.

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. An alternative is the direct reaction of nitrobenzene with aniline via a nucleophilic aromatic substitution of hydrogen (vicarious nucleophilic substitution). 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. == References ==
Source: Wikipedia ↗
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