2Nitroaniline

2-nitroaniline, also known as o-nitroaniline, is an aromatic amine with a nitro substituent at the 2-position of the benzene ring, giving the chemical formula C6H6N2O2. It is primarily used as an intermediate in the synthesis of dyes, pigments, and some pharmaceutical compounds.

Production and isomerism

It is typically produced by nitration of aniline under strongly acidic conditions. Nitration of aniline generates a mixture of ortho- and para-nitroaniline, with the ortho isomer commonly sought for isolation by crystallization or related separation methods.

Properties

2-Nitroaniline appears as a pale yellow crystalline solid and is sparingly soluble in water, with greater solubility in organic solvents. The molecule contains both a nitro group and an amino group, which give it characteristic reactivity suitable for further chemical transformations. It can be chemically reduced to o-phenylenediamine, a versatile intermediate in azo dye synthesis and other applications.

Applications

The primary use of 2-nitroaniline is as a building block in the manufacture of dyes and pigments, including azo dyes. It also serves as an intermediate in the preparation of various organic compounds and pharmaceutical precursors.

Safety

2-Nitroaniline is a hazardous chemical. It can be irritating to skin, eyes, and the respiratory tract and may cause methemoglobinemia if absorbed in significant amounts. It should be handled in a well-ventilated area with appropriate personal protective equipment, and waste must be disposed of as hazardous material in accordance with regulations.