Trimethylsilylacetylene

A colorless liquid, "tms acetylene", as it is also called, is used as a source of "HC2−" in organic synthesis.

Using this protected alkyne, as opposed to acetylene itself, prevents further coupling reactions.

The trimethylsilyl group can then be cleaved off with TBAF or DBU to form phenylacetylene derivatives.

It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride.

He reduced chloro(trimethylsilyl)acetylene by reaction with phenyllithium in diethyl ether and proceeded with subsequent hydrolysis.