Potassium thioacetate is an organosulfur compound and a salt with the formula CH3COS−K+. This white, water-soluble solid is used as a reagent for preparing thioacetate esters and other derivatives.
Synthesis and reactions Potassium thioacetate, which is commercially available, can be prepared by combining acetyl chloride and potassium hydrosulfide:
CH3COCl + 2 KSH → KCl + CH3COSK + H2S It arises also by the neutralisation of thioacetic acid with potassium hydroxide.
Use in preparation of thiols In a common application, potassium thioacetate is combined with alkylating agents to give thioacetate esters (X = halide):
CH3COSK + RX → CH3COSR + KX One example is ethyl thioacetate. Hydrolysis of these esters affords thiols:
CH3COSR + H2O → CH3CO2H + RSH The thioacetate esters can also undergo cleavage with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of pent-4-yne-1-thiol:
H3C(CH2)3OMs + KSAc → H3C(CH2)3SAc + KOMs H3C(CH2)3SAc + HSMe → H3C(CH2)3SH + MeSAc
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