2Mercaptoaniline

2-Mercaptoaniline, also known as 2-aminothiophenol, is an organic compound with the chemical formula C6H7NS. It is an aromatic amine and a thiol, featuring both an amino group (-NH2) and a sulfhydryl group (-SH) attached to a benzene ring in ortho positions (adjacent carbons). This compound is a pale yellow solid with a characteristic odor.

2-Mercaptoaniline is soluble in organic solvents like ethanol and ether but has limited solubility in water. It is an important intermediate in the synthesis of various heterocyclic compounds, particularly benzothiazoles. These heterocyclic structures find applications in pharmaceuticals, dyes, and agrochemicals. The reactivity of the amino and sulfhydryl groups allows for cyclization reactions to form these fused ring systems.

The compound can be synthesized through several methods, often involving the reduction of nitrobenzenesulfonyl chloride or related derivatives. Due to its reactive functional groups, 2-mercaptoaniline can undergo oxidation, for instance, to form disulfides. Its handling requires appropriate safety precautions due to its potential toxicity and unpleasant odor. Research continues to explore new applications and synthetic routes for this versatile chemical.