2mercaptobenzoic

2-Mercaptobenzoic acid, also known as thiosalicylic acid, is an organosulfur compound with the chemical formula C7H6O2S. It is a derivative of benzoic acid where a thiol group (-SH) is attached at the ortho position (position 2) relative to the carboxylic acid group (-COOH). This compound exists as a white to pale yellow crystalline solid.

The presence of both a carboxylic acid and a thiol group makes 2-mercaptobenzoic acid a bifunctional molecule, capable of participating in reactions characteristic of both functional groups. The thiol group can undergo oxidation, form disulfide bonds, and act as a nucleophile. The carboxylic acid group can undergo esterification, amide formation, and salt formation.

2-Mercaptobenzoic acid finds applications in various fields. It is used as a chelating agent, forming stable complexes with metal ions. This property makes it useful in analytical chemistry for the detection and quantification of certain metals. It also serves as a building block in the synthesis of more complex organic molecules, including pharmaceuticals and agrochemicals. In some cases, it has been explored for its potential antioxidant properties due to the presence of the thiol group, which can scavenge free radicals. Its synthesis typically involves the reaction of anthranilic acid with sodium nitrite and potassium ethyl xanthate, followed by hydrolysis.