Potassium thioacetate
Organosulfur compound (CH3COS- K+)
From Wikipedia, the free encyclopedia
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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| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.030.759 |
| EC Number |
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| MeSH | C005732 |
PubChem CID |
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| UNII | |
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
Potassium thioacetate, which is commercially available, can be prepared by combining acetyl chloride and potassium hydrosulfide:
- CH3COCl + 2 KSH → KCl + CH3COSK + H2S
It arises also by the neutralisation 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 undergo cleavage 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