2aminothiophenols

2-Aminothiophenol, also known as 2-mercaptoaniline or o-aminothiophenol, is an organic compound with the chemical formula C6H7NS. It is a derivative of aniline where one hydrogen atom on the benzene ring at the ortho position (adjacent to the amino group) is replaced by a thiol group (-SH). This compound exists as a pale yellow to brown liquid or solid, depending on its purity and temperature, and possesses a characteristic strong odor.

The presence of both an amine (-NH2) and a thiol (-SH) functional group makes 2-aminothiophenol a versatile molecule in organic synthesis. It readily undergoes reactions characteristic of both amines and thiols. For instance, the amino group can be acylated or alkylated, while the thiol group can be oxidized or react with electrophiles.

2-Aminothiophenol is an important precursor in the synthesis of various heterocyclic compounds. It is particularly useful in the formation of benzothiazoles, which are a class of sulfur and nitrogen-containing heterocycles with applications in pharmaceuticals, dyes, and rubber accelerators. The reaction typically involves condensation with carboxylic acids or their derivatives.

Due to its reactivity, 2-aminothiophenol can be sensitive to oxidation, especially in the presence of air, leading to the formation of disulfide dimers. It should be handled with appropriate safety precautions, as it can be irritating to skin and eyes, and its vapors may be harmful. Storage is often recommended under an inert atmosphere to prevent degradation.