3D model (JSmol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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
- CH3COCl + 2 KSH → KCl + CH3COSK + H2S
It arises also by the neutralization of thioacetic acid with potassium hydroxide.
Use in preparation of thiols
- CH3COSK + RX → CH3COSR + KX (X = halide)
Hydrolysis of these esters affords thiols:
- CH3COSR + H2O → CH3CO2H + RSH
The thioacetate esters can also be cleaved with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of 4-pentyne-1-thiol:
- HC2(CH2)3OMs + KSAc → HC2(CH2)3SAc + KOMs
- HC2(CH2)3SAc + HSMe → HC2(CH2)3SH + MeSAc