Dithiobenzoic acid is the

organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

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. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which ...

, but more acidic and deeply colored.

Synthesis and reactions

It can be prepared by sulfiding

benzotrichloride Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinat ...

: :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 forms colorless crystals. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide i ...

with

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as ...

, 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, a thioacyl chloride is an organic compound containing the functional group . Their formula is usually written , where R is a side chain. Thioacyl chlorides are analogous to acyl chlorides, but much rarer and less robust. Ind ...

C₆H₅C(S)Cl. DTBNIT11

References

Organic acids Organosulfur compounds