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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.
Additional recommended knowledge
The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:
((CH3)3Si)2S must be protected from air because it hydrolyzes readily:
(tms)2S is primarily used to convert oxides and chlorides into the corresponding sulfides. This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is:
In a similar way, it has been used in the conversion of aldehydes and ketones to the corresponding thiones.
((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.
Categories: Organosilicon compounds | Sulfur compounds
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bis(trimethylsilyl)sulfide". A list of authors is available in Wikipedia.|