Triethylsilane Explained

Triethylsilane is the organosilicon compound with the formula (C₂H₅)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.^[1] 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 is used in organic synthesis as a reducing agent and as a precursor to silyl ethers.^[2] As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.^[3]

Additional reading

• • Über Siliziumpropylverbindungen. Pape C.. Ber. 14. 1873 . 1881.
• The Chemistry of the Triethylsilicyl Group. Charles A. Kraus . Walter K. Nelson . amp . J. Am. Chem. Soc.. 56. 1. 195–202 . 1934 . 10.1021/ja01316a062.

Notes and References

1. Ladenburg . A. . 1872 . Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate . Justus Liebigs Annalen der Chemie . de . 164 . 2 . 300–332 . 10.1002/jlac.18721640212 . 0075-4617.
2. Book: 10.1002/9780470842898.rt226.pub2. Triethylsilane. Encyclopedia of Reagents for Organic Synthesis. 2007. Fry. James L.. Rahaim. Ronald J.. Maleczka. Robert E.. 978-0471936237.
3. 10.1021/ja00059a008. Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: Direct evidence for a silyl migration pathway. 1993. Brookhart. M.. Grant. B. E.. Journal of the American Chemical Society. 115. 6. 2151–2156.