Dithiobenzoic acid is the

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulf ...

with the formula C₆H₅CS₂H. It is a

dithiocarboxylic acid Dithiocarboxylic acids are organosulfur compounds with the formula . They are the dithia analogues of carboxylic acids. A closely related and better studied family of compounds are the monothiocarboxylic acids, with the formula . Dithiocarboxyli ...

, 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, w ...

, but more acidic and deeply colored.

Synthesis and reactions

It can be prepared by sulfiding

benzal 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 ...

: :C₆H₅CCl₃ + 4 KSH → C₆H₅CS₂K + 3 KCl + 2 H₂S :C₆H₅CS₂K + H⁺ → C₆H₅CS₂H + K⁺ It also arises by the reaction of the Grignard reagent

phenylmagnesium bromide Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It i ...

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 ...

, followed by acidification: :C₆H₅MgBr + CS₂ → C₆H₅CS₂MgBr :C₆H₅CS₂MgBr + HCl → C₆H₅CS₂H + MgBrCl It is about 100x more acidic than

. 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 In organic chemistry, thioacyl chloride is a functional group of the type RC(S)Cl, where R is an organic substituent. Thioacyl chlorides are analogous to acid chlorides, but much rarer and less robust. The best studied is thiobenzoyl chloride, a ...

C₆H₅C(S)Cl. DTBNIT11

References

Organic acids Organosulfur compounds