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Dithiobenzoic acid is the organosulfur compound with the formula C6H5CS2H. It is a dithiocarboxylic acid, an analogue of
benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, ...
, but more acidic and deeply colored.
Synthesis and reactions
It can be prepared by sulfidingbenzal chloride
Benzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis.
Preparation and usage
Benzal chloride is produced by the free radical chlorination o ...
:
: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
Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical n ...
, followed by acidification:
:C6H5MgBr + CS2 → C6H5CS2MgBr
:C6H5CS2MgBr + HCl → C6H5CS2H + MgBrCl
It is about 100x more acidic than benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, ...
. Its conjugate base, dithiobenzoate, undergoes S-alkylation to give dithiocarboxylate esters. 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