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]
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.030.759 |
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| MeSH | C005732 |
PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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Synthesis and reactions
editPotassium 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
editIn 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
edit- ^ 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. ISBN 978-0-471-93623-7.