Triethylsilane


Triethylsilane, also known as TES or triethylsilicon hydride, is the organosilicon compound with the formula 3SiH. It is a trialkylsilane. The Si-H bond is reactive.
It was first discovered by Albert Ladenburg in 1872 among the products of reduction of tetraethyl orthosilicate with sodium and diethylzinc. He also prepared it by a stepwise reduction via ethoxytriethylsilane and named it silicoheptyl hydride, reflecting the idea of a silicon compound analogous to a seven-carbon hydrocarbon. This colorless liquid finds occasion use in organic synthesis. As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.

Organic chemistry

Triethylsilane is an occasional reagent in organic synthesis. In combination with indium compounds, it reduces esters to ethers. The reaction is typically performed in chloroform at 60 °C, using 0.05 equivalents of InBr3 catalyst. This system can also accommodate other carbonyl compounds like tertiary amides and carboxylic acids.

Additional reading

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