4-Nitrotoluene
4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. This compound is mainly used to prepare dyes.
Synthesis and reactions
Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene. It undergoes the expected reactions, e.g. hydrogenation gives p-toluidine.
Applications
The principle application involves its sulfonation to give the 4-nitrotoluene-2-sulfonic acid (SO3H group adjacent to methyl). This species is produced on a large scale since it can be coupled to make stilbene derivatives which are used as dyes. Representative derivatives include 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids.
Safety
There is some evidence for toxicity and carcinogenecity in mice.
References
External links
CDC - NIOSH Pocket Guide to Chemical Hazards - p-Nitrotoluene