Bis(trimethylsilyl)sulfide

Bis(trimethylsilyl)sulfide is a chemical compound with the formula ((CH3)3Si)2S. It is a colorless liquid that is used as a reagent in organic synthesis. The compound is a derivative of sulfide and contains two trimethylsilyl groups.

Structure and Bonding

Bis(trimethylsilyl)sulfide is a covalent compound that consists of a central sulfur atom bonded to two trimethylsilyl groups. The sulfur atom is in the -2 oxidation state, and the silicon atoms are in the +4 oxidation state. The molecule has a bent structure, similar to that of water, due to the presence of two lone pairs of electrons on the sulfur atom.

Synthesis

Bis(trimethylsilyl)sulfide can be synthesized by the reaction of chlorotrimethylsilane with sodium sulfide in an aprotic solvent such as dimethylformamide (DMF). The reaction proceeds via a nucleophilic substitution mechanism.

Applications

In organic synthesis, bis(trimethylsilyl)sulfide is used as a silylating agent to protect functional groups such as alcohols and amines. The trimethylsilyl groups can be easily removed under mild conditions, making them useful for temporary protection during multi-step synthesis.

Safety

Like many organosilicon compounds, bis(trimethylsilyl)sulfide is flammable and should be handled with care. It can also cause irritation to the skin and eyes.

See also

• Trimethylsilyl chloride
• Sodium sulfide
• Silylation