Orthomercaptoaniline

Ortho-mercaptoaniline, also known as 2-aminothiophenol, is an organic compound with the chemical formula C6H7NS. It is characterized by the presence of both an amine group (-NH2) and a thiol group (-SH) attached to adjacent carbon atoms on a benzene ring. This ortho-substitution pattern is key to its chemical properties.

This compound typically appears as a colorless to yellow liquid or low-melting solid. It is soluble in many organic solvents and has a distinct, often unpleasant, odor characteristic of thiols. The dual functionality of the amine and thiol groups makes ortho-mercaptoaniline a versatile building block in organic synthesis. It readily participates in reactions involving both functional groups, such as cyclization reactions to form heterocyclic compounds.

Ortho-mercaptoaniline is used as a reagent in the synthesis of various heterocyclic compounds, including benzothiazoles, which find applications in dyes, pharmaceuticals, and rubber accelerators. It can also be employed in the preparation of metal complexes due to the chelating ability of its amine and thiol groups. The compound is sensitive to oxidation, particularly in the presence of air, which can lead to the formation of disulfide derivatives. Proper handling and storage under inert atmosphere are often recommended to maintain its purity and reactivity.