Potassium thioacetate

Potassium thioacetate
Identifiers
CAS Number	10387-40-3;
3D model (JSmol)	Interactive image;
ChemSpider	74542;
EC Number	233-848-7;
MeSH	C005732
PubChem CID	4463282;
	InChI InChI=1S/C2H4OS.K/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Key: AFNBMGLGYSGFEZ-UHFFFAOYSA-M;
	SMILES CC(=S)[O-].[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:

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

Zongjun Qiao and Xuefeng Jiang "Potassium Thioacetate" e-EROS Encyclopedia Of Reagents For Organic Synthesis, 2014. doi:10.1002/047084289X.rn01737
Matteo Minozzi, Daniele Nanni, Piero Spagnolo (2008). "4-Pentyne-1-thiol". eEROS. doi:10.1002/047084289X.rn00855.CS1 maint: uses authors parameter (link)

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[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.CS1 maint: uses authors parameter (link)