2,4-Diaminotoluene

2,4-Diaminotoluene is an aromatic organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid, although commercial samples are often yellow-tan.

Preparation
It is prepared by hydrogenation of 2,4-dinitrotoluene using a nickel catalyst. Commercial samples often contain up to 20% of the 2,6-isomer.

A laboratory method involves reduction of 2,4-dinitrotoluene with iron powder.

Use
It is mainly used to manufacture toluene diisocyanate, which is a key raw material in polyurethane chemistry. It is still the starting material used when non-phosgene methods of production of toluene diisocyanate are used.

It is also a degradation product of polyurethane materials produced using toluene diisocyanate.



Its reaction with benzenediazonium chloride gives the cationic azo dye Basic Orange 1. Condensation of 2,4-diaminotoluene with acetaldehyde gives the acridine dye called Basic Yellow 9.

Toxicity
Aromatic amines in general often are classed as toxic and so the toxicity profile of this species has been studied. It has received more in depth study in the 21st century.