Dithiobenzoic acid

Dithiobenzoic acid is the organosulfur compound with the formula C₆H₅CS₂H. It is a dithiocarboxylic acid, an analogue of benzoic acid, but more acidic and deeply colored.

Synthesis and reactions

It can be prepared by sulfiding benzotrichloride:
It also arises by the reaction of the Grignard reagent phenylmagnesium bromide with carbon disulfide, followed by acidification:
It is about 100x more acidic than benzoic acid. Its conjugate base, dithiobenzoate, undergoes S-alkylation to give dithiocarboxylate esters. Similarly, dithiobenzoate reacts with "soft" metal salts to give complexes, e.g. Fe₃ and Ni₂.
Chlorination of dithiobenzoic acid gives the thioacyl chloride C₆H₅CCl.