Potassium thioacetate

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Potassium thioacetate
KSAc.png
Identifiers
3D model (JSmol)
ChemSpider
EC Number 233-848-7
MeSH C005732
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).
Infobox references

Potassium thioacetate is an organosulfur compound and a salt with the formula CH3COSK+. This white, water-soluble solid is used as a reagent for preparing thioacetate esters and other derivatives.[1]

Synthesis and reactions[edit]

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[edit]

In a common application, potassium thioacetate is combined with alkylating agents to give thioacetate esters:

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:[2]

HC2(CH2)3OMs + KSAc → HC2(CH2)3SAc + KOMs
HC2(CH2)3SAc + HSMe → HC2(CH2)3SH + MeSAc

References[edit]

  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.