2-Nitrotoluene or ''ortho''-nitrotoluene is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃C₆H₄NO₂. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

Synthesis and reactions

It is made by nitrating

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

at above -10 °C. This reaction affords a 2:1 mixture of 2-nitro and 4-nitro isomers. Chlorination of 2-nitrotoluene gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene. 2-Nitrotoluene is mainly consumed in the production of

o-toluidine ''o''-Toluidine (''ortho''-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precu ...

, a precursor to dyes.

References

External links

CDC - NIOSH Pocket Guide to Chemical Hazards - o-Nitrotoluene
Nitrotoluenes 2-Tolyl compounds {{aromatic-stub