3-Nitroaniline


3-Nitroaniline, also known as meta-nitroaniline and m-nitroaniline, is a non-volatile stable solid commonly used as a raw material for dyes. 3-Nitroaniline is an aniline carrying a nitro functional group in position 3. It is stable in neutral, acidic or alkaline solutions and is classified as "not readily biodegradable" with "low bioaccumulation potential".
It is used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances during the dyeing process.

Synthesis

It can be synthesized by nitration of benzamide followed by the Hofmann rearrangement of the 3-nitrobenzamide previously formed. It consist in treating the 3-nitrobenzamide with sodium hypobromite or sodium hypochlorite to transform the amide group into an amine.