2,5-Xylidine

2,5-Xylidine is an organic compound with the formula C₆H₃(CH₃)₂NH₂. It is one of several isomeric xylidines. It is a colorless viscous liquid. Commercially significant derivatives include Solvent Yellow 30, Solvent Red 22, Acid Red 65, and Solvent Red 26.

File:Solvent Red 26.png

Solvent Red 26 is a commercial dye prepared from 2,5-xylidine

Production

Like many xylidines, it is prepared by nitration of the corresponding xylene followed by reduction of the nitroxylene. Reduction can be effected with HCl/Fe, but usually is achieved by catalytic hydrogenation:

Me₂C₆H₄ + HNO₃ → Me₂C₆H₃NO₂ + H₂O

Me₂C₆H₃NO₂ + 3 H₂ → Me₂C₆H₃NH₂ + 3H₂O

Safety

It is mutagenic and tumor-inducing. Acute toxicity of xylidines is modest as indicated by LD50 (rats, oral) are in the range 0.1-1 g/kg.