{{chembox |Watchedfields = changed |verifiedrevid = 404977195 |ImageFile = Triethylsilane Structural Formula V1.svg |ImageAlt = Skeletal formula of triethylsilane |ImageFile1 = Triethylsilane-3D-balls.png |ImageSize1 = 180 |ImageAlt1 = Ball-and-stick model of the triethylsilane molecule |PIN = Triethylsilane |Section1={{Chembox Identifiers |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 617-86-7 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 0F9429873L |EC_number = 210-535-3 |PubChem = 12052 |ChemSpiderID = 11555 |SMILES = CC[SiH](CC)CC |StdInChI = 1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3 |StdInChIKey = AQRLNPVMDITEJU-UHFFFAOYSA-N }} |Section2={{Chembox Properties |Formula = C<sub>6</sub>H<sub>16</sub>Si |MolarMass = 116.28 g/mol |Appearance = colorless liquid |Density = 0.728 g/mL |LogP = 3.08 |MeltingPtC = -156.1 |BoilingPtC = 107 - 108 |BoilingPt_notes = |VaporPressure = 31 hPa at 20 °C<br>75 hPa at 38 °C<br>126 hPa at 50 °C }} |Section3={{Chembox Hazards |GHSPictograms = {{GHS02}} |GHSSignalWord = Danger |HPhrases = {{H-phrases|225|412}}<ref name="sigma">{{Sigma-Aldrich|id=230197|name=Triethylsilane|accessdate=2015-01-30}}</ref> |PPhrases = {{P-phrases|210|273}}<ref name="sigma" /> |FlashPtC = -2.99 |FlashPt_notes = closed cup<ref name="sigma" /> }} }}
'''Triethylsilane''' , also known as TES or triethylsilicon hydride, is the organosilicon compound with the formula (C<sub>2</sub>H<sub>5</sub>)<sub>3</sub>SiH. 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.<ref>{{Cite journal |last=Ladenburg |first=A. |date=1872 |title=Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate |url=https://books.google.com/books?id=HNXyAAAAMAAJ&pg=RA2-PA300 |journal=Justus Liebigs Annalen der Chemie |language=de |volume=164 |issue=2 |pages=300–332 |doi=10.1002/jlac.18721640212 |issn=0075-4617}}</ref> 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.<ref>{{cite book|doi=10.1002/9780470842898.rt226.pub2|chapter=Triethylsilane|title=Encyclopedia of Reagents for Organic Synthesis|year=2007|last1=Fry|first1=James L.|last2=Rahaim|first2=Ronald J.|last3=Maleczka|first3=Robert E.|isbn=978-0471936237}}</ref> As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.<ref>{{cite journal |doi=10.1021/ja00059a008|title=Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: Direct evidence for a silyl migration pathway|year=1993|last1=Brookhart|first1=M.|last2=Grant|first2=B. E.|journal=Journal of the American Chemical Society|volume=115|issue=6|pages=2151–2156 |bibcode=1993JAChS.115.2151B }}</ref>
==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 InBr<sub>3</sub> catalyst.<ref name=":0">{{Cite journal |last1=Sakai |first1=Norio |last2=Moriya |first2=Toshimitsu |last3=Fujii |first3=Kohji |last4=Konakahara |first4=Takeo |date=November 2008 |title=Direct Reduction of Esters to Ethers with an Indium(III) Bromide/Triethylsilane Catalytic System |url=http://www.thieme-connect.de/DOI/DOI?10.1055/s-0028-1083191 |journal=Synthesis |language=en |volume=2008 |issue=21 |pages=3533–3536 |doi=10.1055/s-0028-1083191 |issn=0039-7881|url-access=subscription }}</ref><ref name=":4">{{Cite web |title=Synthesis of Ethers from Carbonyl Compounds by Reductive Etherification Catalyzed by Iron(III) and Silyl Chloride |url=https://www.organic-chemistry.org/abstracts/lit4/995.shtm |access-date=2026-01-12 |website=www.organic-chemistry.org}}</ref> This system can also accommodate other carbonyl compounds like tertiary amides and carboxylic acids.<ref>{{Cite web |title=An Efficient One-Pot Synthesis of Unsymmetrical Ethers: A Directly Reductive Deoxygenation of Esters Using an InBr3/Et3SiH Catalytic System |url=https://www.organic-chemistry.org/abstracts/lit1/800.shtm |access-date=2026-01-12 |website=www.organic-chemistry.org}}</ref>
== Additional reading == * {{OrgSynth | author = Richard T. Beresis, Jason S. Solomon, Michael G. Yang, Nareshkumar F. Jain, and James S. Panek | title = <nowiki>Synthesis of Chiral (E)-Crotylsilanes: [3R- AND 3S-]-(4E)-Methyl 3-(Dimethylphenylsilyl)-4-Hexenoate </nowiki> | volume = 75 | pages = 78 | year = 1998 | prep = v75p0078}} * {{OrgSynth | author = Alessandro Dondoni and Daniela Perrone | title = <nowiki>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 </nowiki> | volume = 77 | pages = 78 | year = 2000 | prep = v77p0078}} *{{cite journal | title = Über Siliziumpropylverbindungen | author = Pape C. | journal = Ber | volume = 14 | pages = 1873 | year = 1881 | url = http://gallica.bnf.fr/ark:/12148/bpt6k906939/f283.chemindefer }} *{{cite journal | title = The Chemistry of the Triethylsilicyl Group |author1=Charles A. Kraus |author2=Walter K. Nelson |name-list-style=amp | journal = J. Am. Chem. Soc. | volume = 56 | issue = 1 | pages = 195–202 | year = 1934 | doi = 10.1021/ja01316a062 |bibcode=1934JAChS..56..195K }}
==References== {{Reflist}}
Category:Reducing agents Category:Carbosilanes