Potassium thioacetate

Potassium thioacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.030.759 Edit this at Wikidata
EC Number
  • 233-848-7
MeSH C005732
UNII
  • InChI=1S/C2H4OS.K/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
    Key: AFNBMGLGYSGFEZ-UHFFFAOYSA-M
  • CC(=O)[S-].[K+]
Properties
C2H3KOS
Molar mass 114.21
Appearance white solid
good
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.[1]

Synthesis and reactions

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

CH3COCl + 2 KSH → KCl + CH3COSK + H2S

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):

CH3COSK + RX → CH3COSR + KX

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 pent-4-yne-1-thiol:[2]

H3C(CH2)3OMs + KSAc → H3C(CH2)3SAc + KOMs
H3C(CH2)3SAc + HSMe → H3C(CH2)3SH + MeSAc

References

  1. ^ Zongjun Qiao and Xuefeng Jiang "Potassium Thioacetate" e-EROS Encyclopedia Of Reagents For Organic Synthesis, 2014. doi:10.1002/047084289X.rn01737
  2. ^ Matteo Minozzi; Daniele Nanni; Piero Spagnolo (2008). "4-Pentyne-1-thiol". EEROS. doi:10.1002/047084289X.rn00855. ISBN 978-0-471-93623-7.