Related compounds Boiling point 162 °C | Density 846 kg/m³ | |
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Appearance colourless liquid with foul odor | ||
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.
Contents
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 + H2SUse in synthesis
Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides. This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is:
((CH3)3Si)2S + MO → ((CH3)3Si)2O + MSIn 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.