Triethylsilane

Triethylsilane is the organosilicon compound with the formula (C2H5)3SiH. It is a trialkylsilane. The Si-H bond is reactive. 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]

Triethylsilane
Skeletal formula of triethylsilane
Ball-and-stick model of the triethylsilane molecule
Names
Preferred IUPAC name
Triethylsilane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.579 Edit this at Wikidata
EC Number
  • 210-535-3
UNII
  • InChI=1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3
    Key: AQRLNPVMDITEJU-UHFFFAOYSA-N
  • CC[SiH](CC)CC
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:
GHS02: Flammable
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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Additional readingEdit

  • 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. doi:10.1021/ja01316a062.

ReferencesEdit

  1. ^ a b c Sigma-Aldrich Co., Triethylsilane. Retrieved on 2015-01-30.
  2. ^ Fry, James L.; Rahaim, Ronald J.; Maleczka, Robert E. (2007). "Triethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rt226.pub2. ISBN 978-0471936237.
  3. ^ Brookhart, M.; Grant, B. E. (1993). "Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: Direct evidence for a silyl migration pathway". Journal of the American Chemical Society. 115 (6): 2151–2156. doi:10.1021/ja00059a008.