page_title: Dithiobenzoic acid
section_title: Synthesis and reactions
hierarchical_section_title: Dithiobenzoic acid / Synthesis and reactions
caption_attribution_description: English: portion of the polymer [Ni(S2CPh)2]n.
context_page_description: 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.
context_section_description: It can be prepared by sulfiding benzal chloride: 
  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:
  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.  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.
caption: Structure of the trimer [Ni(S2CPh)2]3.[4]
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