Triethylsilane

Triethylsilane

Names
Preferred IUPAC name Triethylsilane
Identifiers
CAS Number	617-86-7  Y
3D model (JSmol)	Interactive image
ChemSpider	11555
ECHA InfoCard	100.009.579
EC Number	210-535-3
PubChem CID	12052
UNII	0F9429873L  Y
CompTox Dashboard (EPA)	DTXSID20870702
InChI InChI=1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3 Key: AQRLNPVMDITEJU-UHFFFAOYSA-N
SMILES CC[SiH](CC)CC
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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H412 [1]
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). Y  verify  (what is  YN ?) Infobox references

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.

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.
• 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.

References

1. Sigma-Aldrich Co., Triethylsilane. Retrieved on 2015-01-30.
2. Ladenburg, A. (1872). "Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate". Justus Liebigs Annalen der Chemie (in German). 164 (2): 300–332. doi:10.1002/jlac.18721640212. ISSN   0075-4617.
3. 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.
4. 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. Bibcode:1993JAChS.115.2151B. doi:10.1021/ja00059a008.
5. Sakai, Norio; Moriya, Toshimitsu; Fujii, Kohji; Konakahara, Takeo (November 2008). "Direct Reduction of Esters to Ethers with an Indium(III) Bromide/Triethylsilane Catalytic System". Synthesis. 2008 (21): 3533–3536. doi:10.1055/s-0028-1083191. ISSN   0039-7881.
6. "Synthesis of Ethers from Carbonyl Compounds by Reductive Etherification Catalyzed by Iron(III) and Silyl Chloride". www.organic-chemistry.org. Retrieved 2026-01-12.
7. "An Efficient One-Pot Synthesis of Unsymmetrical Ethers: A Directly Reductive Deoxygenation of Esters Using an InBr3/Et3SiH Catalytic System". www.organic-chemistry.org. Retrieved 2026-01-12.