Benzidine

Conversion of benzidine to the bis(diazonium) salt was once an integral step in the preparation of direct dyes (requiring no mordant).

Treatment of this bis(diazonium) salt with 1-aminonaphthalene-4-sulfonic acid gives the once popular congo red dye.

A variety of derivatives of 4,4’-benzidine are commercially produced on the scale of one to a few thousand kilograms per year, mainly as precursors to dyes and pigments.

[3] These derivatives include, in order of scale, the following: As with some other aromatic amines such as 2-naphthylamine, benzidine has been significantly withdrawn from use in most industries because it is so carcinogenic.

[7] The manufacture of Benzidine has been illegal in the UK since at least 2002 under the Control of Substances Hazardous to Health Regulations 2002 (COSHH).

Skeletal formula of benzidine
Ball-and-stick model of the benzidine molecule
The popular dye congo red is derived from benzidine.