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.
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Preferred IUPAC name
Benzenecarbodithioic acid | |
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ECHA InfoCard | 100.004.084 |
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Properties | |
C7H6S2 | |
Molar mass | 154.25 g·mol−1 |
Appearance | dark red sticky solid or viscous oil |
Acidity (pKa) | 1.92[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It can be prepared by sulfiding benzal chloride:[2]
It also arises by the reaction of the Grignard reagent phenylmagnesium bromide with carbon disulfide, followed by acidification:[3]
It is about 100x more acidic than benzoic acid. Its conjugate base, dithiobenzoate, undergoes S-alkylation to give dithiocarboxylate esters.[2] Similarly, dithiobenzoate reacts with "soft" metal salts to give complexes, e.g. Fe(S2CC6H5)3 and Ni(S2CC6H5)2.
Chlorination of dithiobenzoic acid gives the thioacyl chloride C6H5C(S)Cl.