Potassium thioacetate explained

Potassium thioacetate is an organosulfur compound and a salt with the formula . This white, water-soluble solid is used as a reagent for preparing thioacetate esters and other derivatives.[1]

Synthesis and reactions

Potassium thioacetate, which is commercially available, can be prepared by combining acetyl chloride and potassium hydrogen sulfide:

It arises also by the neutralization 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):

Hydrolysis of these esters affords thiols:

The thioacetate esters can also be cleaved with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of pent-4-yne-1-thiol:[2]

References

  1. Zongjun Qiao and Xuefeng Jiang "Potassium Thioacetate" e-EROS Encyclopedia Of Reagents For Organic Synthesis, 2014.
  2. 4-Pentyne-1-thiol. Matteo Minozzi . Daniele Nanni . Piero Spagnolo . 2008. 10.1002/047084289X.rn00855. EEROS. 978-0-471-93623-7 .