Triethylsilane Chemical Properties
- Melting point:
- Boiling point:
- 107-108 °C (lit.)
- 0.728 g/mL at 25 °C (lit.)
- vapor pressure
- >1 hPa (20 °C)
- refractive index
- Flash point:
- 25 °F
- storage temp.
- Specific Gravity
- Water Solubility
- Miscible with water.
- Moisture Sensitive
- Hydrolytic Sensitivity
- 3: reacts with aqueous base
- Stable, but moisture sensitive. Highly flammable. Generates highly flammable gas (hydrogen) in contact with water, acids and bases.
- CAS DataBase Reference
- 617-86-7(CAS DataBase Reference)
- NIST Chemistry Reference
- Silane, triethyl-(617-86-7)
- EPA Substance Registry System
- Triethylsilane (617-86-7)
Triethylsilane Usage And Synthesis
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.
- R. Boukherroub,†,‡, C. Chatgilialoglu,,§ and, and G. Manuel†. "PdCl2-Catalyzed Reduction of Organic Halides by Triethylsilane." Organometallics 15.5(1996):1508-1510.
- Jian Yang and, and M. Brookhart. "Iridium-Catalyzed Reduction of Alkyl Halides by Triethylsilane." Journal of the American Chemical Society 129.42(2007):12656-7.
- And, Pijus K. Mandal, and J. S. Mcmurray. "Pd−C-Induced Catalytic Transfer Hydrogenation with Triethylsilane." Journal of Organic Chemistry 72.17(2007):6599-6601.
- Chen, Bang Chi, et al. "Novel triethylsilane mediated reductive N -alkylation of amines: improved synthesis of 1-(4-imidazolyl)methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors." Tetrahedron Letters 42.7(2001):1245-1246.
Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. Triethylsilane is also used as an effective reducing agent.
Triethylsilane is used as a reducing agent inmany organic synthetic reactions.
Highly flammable; flash point －4°C (25°F)
It does not ignite spontaneously in air, but it can explode on heating. The ease of oxidation of this compound is relatively lower than mono- and dialkylsilanes. Reaction with oxidizing substances, however, can be violent. Reaction with boron trichloride could be explosive at room temperature. Even at 78°C ( 108°F), mixing these reagents caused pressure buildup and combustion (Matteson 1990).
Reflux triethylsilane over molecular sieves, then distil it. It is passed through neutral alumina before use [Randolph & Wrighton J Am Chem Soc 108 3366 1986]. [Beilstein 4 IV 3895.]
Triethylsilane Preparation Products And Raw materials
- Triethylsilyl trifluoromethanesulfonate
- tert-Butyldimethylsilyl chloride
- Sodium hydride
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