Triethylsilane
Chemical compound
From Wikipedia, the free encyclopedia
Triethylsilane , also known as TES or triethylsilicon hydride, is the organosilicon compound with the formula (C2H5)3SiH. It is a trialkylsilane. The Si-H bond is reactive.
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| Preferred IUPAC name
Triethylsilane | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.009.579 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H16Si | |
| Molar mass | 116.28 g/mol |
| Appearance | colorless liquid |
| Density | 0.728 g/mL |
| Melting point | −156.1 °C (−249.0 °F; 117.0 K) |
| Boiling point | 107–108 °C (225–226 °F; 380–381 K) |
| log P | 3.08 |
| Vapor pressure | 31 hPa at 20 °C 75 hPa at 38 °C 126 hPa at 50 °C |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H225, H412[1] | |
| P210, P273[1] | |
| Flash point | −2.99 °C (26.62 °F; 270.16 K) closed cup[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It was first discovered by Albert Ladenburg in 1872 among the products of reduction of tetraethyl orthosilicate with sodium and diethylzinc.[2] 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.[3] As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.[4]
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.[5][6] This system can also accommodate other carbonyl compounds like tertiary amides and carboxylic acids.[7]
Additional reading
- Richard T. Beresis, Jason S. Solomon, Michael G. Yang, Nareshkumar F. Jain, and James S. Panek (1998). "Synthesis of Chiral (E)-Crotylsilanes: [3R- AND 3S-]-(4E)-Methyl 3-(Dimethylphenylsilyl)-4-Hexenoate ". Organic Syntheses. 75: 78
{{cite journal}}: CS1 maint: multiple names: authors list (link). - Alessandro Dondoni and Daniela Perrone (2000). "Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)-2-[(4S)-N-tert-Butoxycarbonyl-2,2-Dimethyl-1,3,-oxazolidinyl]-2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde ". Organic Syntheses. 77: 78.
- Pape C. (1881). "Über Siliziumpropylverbindungen". Ber. 14: 1873.
- Charles A. Kraus & Walter K. Nelson (1934). "The Chemistry of the Triethylsilicyl Group". J. Am. Chem. Soc. 56 (1): 195–202. Bibcode:1934JAChS..56..195K. doi:10.1021/ja01316a062.