Triethylsilane

Triethylsilane

Identifiers
CAS Number	617-86-7
EC Number	210-535-3
Properties
Chemical formula	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 pictograms
GHS signal word	Danger
GHS hazard statements	H225, H412[1]
GHS precautionary statements	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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Infobox references

Triethylsilane is a silane with the molecular formula C₆H₁₆Si. It is a trialkylsilicon hydride compound with a reactive Si-H bond. This colorless liquid is often used in organic synthesis, specifically for the hydrosilation of olefins to give alkyl silanes. It can also be used as a reducing agent since it has an active hydride.

Synthesis

Triethylsilane can be prepared by the reaction between three equivalents of ethylene and silane. This can be thought to occur by the coordination of ethylene to silicon followed by the nucleophilic olefin capturing the H in one of the Si-H bonds.

3 C₂H₄ + SiH₄ → (C₂H₅)₃SiH

References

1. Sigma-Aldrich Co., Triethylsilane. Retrieved on 2015-01-30.

• 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 ". Org. Synth. 75: 78.
• 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 ". Org. Synth. 77: 78.
• Pape C. (1881). "Über Siliziumpropylverbindungen". Ber 14: 1873.
• Charles A. Kraus and Walter K. Nelson (1934). "The Chemistry of the Triethylsilicyl Group". J. Am. Chem. Soc. 56 (1): 195–202. doi:10.1021/ja01316a062.