Bis(trimethylsilyl) sulfide is the chemical compound with the formula ((CH3)3Si)2S. Often abbreviated (tms)2S, this colourless, vile-smelling liquid is a useful aprotic source of "S2−" in chemical synthesis.
Synthesis The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide: 2 (CH3)3SiCl + Na2S → ((CH3)3Si)2S + 2 NaCl
((CH3)3Si)2S must be protected from air because it hydrolyzes readily: ((CH3)3Si)2S + H2O → ((CH3)3Si)2O + H2S
Use in synthesis Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides.Lee, S. C.; Holm, R. H., "Nonmolecular Metal Chalcogenide/Halide Solids and Their Molecular Cluster Analogues", Angewandte Chemie International Edition in English, 1990, volume 29, pages 840-856. This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is: ((CH3)3Si)2S + MO → ((CH3)3Si)2O + MS In a similar way, it has been used in the conversion of aldehydes and ketones to the corresponding thiones.
Safety ((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.
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