4-Nitrotoluene or ''para''-nitrotoluene is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with the formula CH
3C
6H
4NO
2. It is a pale yellow solid. It is one of three isomers of
nitrotoluene.
Synthesis and reactions
Together with other isomers, 4-nitrotoluene is prepared by
nitration of
toluene,
commonly using
titanium(IV) nitrate.
It undergoes the reactions typical for nitrobenzene derivatives, e.g.
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate org ...
gives
''p''-toluidine.
Oxidation of the methyl substituent of 4-nitrotoluene has been extensively investigated. Depending on the conditions, oxidation yields 4-nitrobenzaldehyde diacetate, 4-nitrobenzenoic acid, and 4,4'-dinitrobibenzyl. Treatment of 4-nitrotoluene with bromine gives the 4-nitrobenzyl bromide.
Applications
The principal application involves its
sulfonation to give the 4-nitrotoluene-2-sulfonic acid (with the
–SO3H group adjacent to methyl). This species can be oxidatively coupled to produce
stilbene derivatives, which are used as dyes. Representative derivatives include the molecular and
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quanti ...
forms of 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids, e.g.
disodium 4,4'-dinitrostilbene-2,2'-disulfonate.
Safety
Evidence exists for toxicity and
carcinogenicity in mice.
References
External links
CDC – NIOSH Pocket Guide to Chemical Hazards – p-Nitrotoluene
{{DEFAULTSORT:Nitrotoluene, 4-
Nitrotoluenes