Dithiobenzoic acid
Chemical compound From Wikipedia, the free encyclopedia
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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Names | |
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Preferred IUPAC name
Benzenecarbodithioic acid | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.004.084 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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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Synthesis and reactions
It can be prepared by sulfiding benzotrichloride:[2]
- C6H5CCl3 + 4 KSH → C6H5CS2K + 3 KCl + 2 H2S
- C6H5CS2K + H+ → C6H5CS2H + K+
It also arises by the reaction of the Grignard reagent phenylmagnesium bromide with carbon disulfide, followed by acidification:[3]
- C6H5MgBr + CS2 → C6H5CS2MgBr
- C6H5CS2MgBr + HCl → C6H5CS2H + MgBrCl
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.

References
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