benzenethiol

Benzenethiol, C6H5SH, is the simplest aryl thiol, also known as thiophenol or phenyl mercaptan, in which a thiol group (-SH) is attached to a benzene ring. It is a colorless to pale yellow liquid at room temperature with a characteristic strong, penetrating odor typical of thiols.

Thiophenol is moderately acidic for an organic compound, with a pKa in water around 6–7; the thiolate anion formed is a good nucleophile and a common ligand in coordination chemistry. It readily oxidizes to form disulfides such as dibenzothiophene derivatives and other sulfur-containing condensates, and it participates in a variety of reactions typical of thiols, including alkylation and coupling to form thioethers and thioesters.

Benzenethiol is produced commercially as a chemical intermediate and precursor to a variety of sulfur-containing compounds. It serves as a building block for thioethers, thioesters, dyes, and pharmaceutical and agrochemical intermediates, and it can be used in organic synthesis to introduce sulfur-containing functionalities into more complex molecules.

Safety and handling: Benzenethiol is corrosive to skin and eyes and can be harmful if inhaled or ingested. It has a strong odor that acts as a warning property. It should be used only in a well-ventilated area, in appropriate containers, with gloves and eye protection, and stored away from oxidizers and heat. Spills should be contained and ventilated; avoid ignition sources.