Potassium thioacetate

Potassium thioacetate

Identifiers
CAS Number	10387-40-3  Y
3D model (JSmol)	Interactive image
ChemSpider	74542
ECHA InfoCard	100.030.759
EC Number	233-848-7
MeSH	C005732
PubChem CID	4463282
UNII	ZY58K327HN  Y
CompTox Dashboard (EPA)	DTXSID0065060
InChI InChI=1S/C2H4OS.K/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Key: AFNBMGLGYSGFEZ-UHFFFAOYSA-M
SMILES CC(=O)[S-].[K+]
Properties
Chemical formula	C2H3KOS
Molar mass	114.21
Appearance	white solid
Solubility in water	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 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

One example is ethyl thioacetate. 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.