Triethylsilane

Base Information

• Chemical Name: Triethylsilane
• CAS No.: 617-86-7
• Molecular Formula: C6H16Si
• Molecular Weight: 116.279
• Hs Code.: 29310095
• European Community (EC) Number: 210-535-3
• NSC Number: 93579
• UNII: 0F9429873L
• DSSTox Substance ID: DTXSID20870702
• Nikkaji Number: J271.180J
• Wikipedia: Triethylsilane
• Mol file: 617-86-7.mol

Synonyms:triethylsilane;Triethylsilanol

Chemical Property of Triethylsilane

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: >1 hPa (20 °C)
• Melting Point: -157 °C
• Refractive Index: n20/D 1.412(lit.)
• Boiling Point: 107.499 °C at 760 mmHg
• Flash Point: 25°F
• PSA: 0.00000
• Density: 0.728g/mLat 25°C(lit.)
• LogP: 2.27320
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: insol H2O; sol hydrocarbons, halocarbons, ethers.
• Water Solubility.: Miscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 115.094302013
• Heavy Atom Count: 7
• Complexity: 25.7

Purity/Quality:

99.0% ^*data from raw suppliers

Triethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38-52/53
• Safety Statements: 9-16-29-33-37/39-26-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: CC[Si](CC)CC
• Description: Triethylsilane is a useful versatile reductant since it has a active hydride. It can be used for mediated the palladium-catalyzed dehalogenation reaction of alkyl or aryl halides, the reduction of primary, secondary, and tertiary chlorides, bromides, and iodides catalyzed by iridium, as well as efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection. It is also specifically for the hydrosilation of olefins to give alkyl silanes. It is also the catalyst for synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain, redox initiated cationic polymerization and Beckmann rearrangement of cyclododecanone oxime as well as regioselective reductive coupling of enones and allenes.
• Uses: Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes. Triethylsilane serves as an exemplar for organosilicon hydride behavior as a mild reducing agent. It is frequently chosen as a synthetic reagent because of its availability, convenient physical properties, and economy relative to other organosilicon hydrides which might otherwise be suitable for effecting specific chemical transformations. This reagent is generally used in these reactions: Hydrosilylations, Silane Alcoholysis, Formation of Singlet Oxygen, Reduction of Acyl Derivatives to Aldehydes, Radical Chain Reductions, Ionic Hydrogenations and Reductive Substitutions(The polar nature of the Si–H bond enables triethylsilane to act as a hydride donor to electron-deficient centers.), Reductive Etherifications and Acetal Reductions, Ether Cleavages, Reductive Couplings and Cyclizations, Aromatic Silylations, Generation of Other Triethylsilyl Reagents, etc. Related Reagents: Phenylsilane–cesium fluoride; tri-n-butylstannane; tricarbonylchloroiridium–diethyl(methyl) silane–carbon monoxide; triethylsilane–trifluoroacetic acid.

Technology Process of Triethylsilane

There total 73 articles about Triethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

triethylmethoxysilane (2117-34-2) → triethylsilane (617-86-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; ethyl bromide; tetraoctyl ammonium bromide; In benzene-d6; at 20 ℃; for 24h; Reagent/catalyst; Solvent;

DOI:10.1039/c9cc01961h

Reference yield: 88.0%

triethylsilyl chloride (994-30-9) → triethylsilane (617-86-7)

Guidance literature:

With sodium tetrahydroborate; In acetonitrile; at 20 ℃; for 0.25h; Inert atmosphere;

Reference yield: 80.0%

trimethoxy(sulfanylmethyl)silane (30817-94-8) + bis(triethylsilyl)mercury (4149-29-5) → triethylsilane (617-86-7) + triethyl(trimethoxysilylmethylthio)silane

Guidance literature:

In benzene; at 50 ℃; for 0.25h;

DOI:10.1007/BF00954119

upstream raw materials:

tetraethoxy orthosilicate

diethylzinc

ethyldichlorosilane

ethylmagnesium chloride

Downstream raw materials:

triethyl-(3-phenyl-propenyloxy)-silane

phenyl-acetic acid triethylsilanyl ester

triethyl(2-methylcyclohex-1-enyloxy)silane

1-<(triethylsilyl)oxy>-3-methylcyclohex-1-ene

Refernces

• 1、 Rhodes, Christopher J.. "First observation of stable primary radical cations tBu3SiH cation radical formed by directed radiolysis of a pure compound: tBu3SiH". . p. 19 - 23. Retrieved 1993.
• 2、 Hajdasz, David J.,Squires, Robert R.. "Hypervalent Silicon Hydrides: SiH5-". . p. 3139 - 3140. Retrieved 1986.
• 3、 van Dalen,van den Berg. "". . p. 277,280, 282. Retrieved 1970.
• 4、 Schuhknecht, Danny,Spaniol, Thomas P.,Maron, Laurent,Okuda, Jun. "Regioselective Hydrosilylation of Olefins Catalyzed by a Molecular Calcium Hydride Cation". supporting information. p. 310 - 314. Retrieved 2019/11/26.
• 5、 Von Grotthuss, Esther,Prey, Sven E.,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias. "Dual Role of Doubly Reduced Arylboranes as Dihydrogen- and Hydride-Transfer Catalysts". supporting information. p. 6082 - 6091. Retrieved 2019/04/17.