Trimethylsulfonium

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Trimethylsulfonium
Trimethylsulfonium.svg
Names
Other names
Trimesium
Identifiers
676-84-6
ChemSpider 1115
Jmol 3D model Interactive image
  • C[S+](C)C
Properties
C3H9S+
Molar mass 77.17 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylsulfonium (systematically named trimethylsulfanium and trimethylsulfur(1+)) is an organic cation with the chemical formula (CH3)3S+ (also written as C
3
H
9
S+
). It is the simplest sulfonium cation.

Compounds

Several salts of trimethylsulfonium are known:

Salt Molecular formula Chemical formula Molecular weight (g/mol) Properties[1]
Trimethylsulfonium chloride (CH3)3SCl C3H9ClS 112.5 Colorless crystals, decompose at 100 °C, very soluble in ethanol, very hygroscopic.[2]
Trimethylsulfonium bromide (CH3)3SBr C3H9BrS 157 Colorless crystals from H2O. Decomposes at 172 °C, melts in a sealed tube at 201-201 °C, reacts in neutral aqueous solution.[3]
Trimethylsulfonium iodide (CH3)3SI C3H9IS 204 Colorless crystals from ethanol, decomposes at 203-207 °C.[3][4]

Preparation

Sulfonium compounds can be synthesised by treating a suitable alkyl halide with a thioether. For example, the reaction of dimethyl sulfide with iodomethane yields trimethylsulfonium iodide:

CH3–S–CH3 + CH3–I → (CH3)3SI

References

  1. Heilbron's Dictionary of Organic Compounds, volume 4, revised edition published in 1953. Published in Great Britain
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See also