Triethylsilane

• Catalog No.: A10320
• CAS Number: 617-86-7
• M. F.: C6H16Si
• M. W.: 116.27674
• Purity: 98+%

SYNONYMS

• Title: 三乙基硅烷
• IUPAC name: triethylsilane
• IUPAC Traditional name: triethylsilane

DATABASE IDS

• Beilstein Number: 1098278
• EC Number: 210-535-3
• MDL Number: MFCD00009018
• CAS Number: 617-86-7

PROPERTIES

• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-36/37/38
• Safety Statements: 9-16-26-33-37-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II
• GHS Hazard statements: H225-H315-H319-H335
• Purity: 98+%
• Boiling Point: 107-108°C
• Density: 0.728
• Flash Point: -6°C(21°F)
• Melting Point: -157°C
• Refractive Index: 1.4120

REFERENCES

• For trans-hydrosilylation of alkynes, catalyzed by AlCl₃, see: J. Org. Chem., 61, 7354 (1996); 64, 2494 (1999).
• For reductive alkylation of indoles, see 2-Methylindole, A10764.
• In combination with TFA, "ionic hydrogenation" of alkenes occurs. This can be a useful alternative to catalytic hydrogenation, since selective reduction, e.g. of the more branched double bond of a diene can be achieved. For a review of ionic hydrogenation, see: Synthesis, 633 (1974):
  
• ɑ?-Enones are reduced selectively to saturated ketones In the presence of TFA: Synthesis, 420 (1973); or Wilkinson's catalyst (Chlorotris(triphenylphosphine)rhodium(I), 10468): Tetrahedron Lett., 5035 (1972); Organometallics, 1, 1390 (1982).
• With TFA, aliphatic ketones are reduced to secondary alcohols, whereas aromatic ketones and aldehydes are further reduced to the hydrocarbons: J. Org. Chem., 38, 2675 (1973). With BF₃, both aliphatic and aromatic carbonyl groups are reduced to the hydrocarbons: J. Org. Chem., 43, 374 (1978); Synth. Commun., 24, 1999 (1994). For selective reduction of a ketone in the presence of a nitro group, see: Org. Synth. Coll., 7, 393 (1990). Reduction of ketones to methylenes also occurs in the presence of TICl₄, allowing the formation of N-protected ɑ-amino acids from keto analogues without racemization: Heterocycles, 41, 17 (1995). For reduction of carbonyl groups catalyzed by B(C₆F₅)₃, see: J. Am. Chem. Soc., 118, 9440 (1996). Reduction of aldehydes, acyl chlorides and esters to methyl groups using this catalyst has been described: J. Org. Chem., 66, 1672 (2001). The polysubstitution and rearrangement encountered with Friedel-Crafts alkylations can be circumvented by an effective one-pot technique employing AlCl₃ acylation followed by in situ reduction withEt₃SiH: J. Chem. Soc., Perkin 1, 1705 (1989). See also Poly(methylhydrosiloxane), L14561, as an alternative reducing agent.
• Silylation of OH groups, with elimination of H₂, occurs with catalysis by TBAF under very mild conditions: Tetrahedron Lett., 35, 8413 (1994); cf Chlorotriethylsilane, A15547. The use of 2-8 mol% Tris(pentafluorophenyl)borane, L18054, has been reported to be more effective than TBAF for the silylation of alcohols and phenols, with secondary and tertiary alcohols reacting faster than primary: J. Org. Chem., 64, 4887 (1999). With excess reagent, reduction of primary alcohols and ethers to methyl occurs: J. Org. Chem., 65, 6179 (2000).
• High-yield, selective hydrodehalogenation of alkyl and aryl halides is catalyzed by PdCl₂, avoiding the skeletal rearrangements of alkyl halides sometimes observed with Lewis acid catalysts such as AlCl₃: Organometallics. 15, 1508 (1996); cf: J. Org. Chem., 41, 1393 (1976).
• Using various Pt group catalysts, acyl halides can be reduced to aldehydes, as an alternative to the Rosenmund reduction. For examples, see: Org. Prep. Proced. Int., 12, 13 (1980). For reduction of nitriles to aldehydes, see: Triethyloxonium tetrafluoroborate, A14420. Nitroarenes can be reduced to anilines using Wilkinson's Catalyst: Synth. Commun., 26, 973 (1996).
• In the presence of Ti(O-i-Pr)₄, phosphine oxides can be reduced to phosphines, a useful alternative to pyrophoric HSiCl₃: Tetrahedron Lett., 35, 625 (1994).
• For use as a superior cation scavenger in peptide synthesis, see Triisopropylsilane, L09585.
• Aryl halides have been silylated using PtO₂ as a catalyst, to give aryltriethylsilanes: Org. Let.., 8, 931 (2006).
• In combination with indium(III) chloride and a radical initiator, generates a radical reagent, analogous to Tri-n-butyltin hydride, A13298, which effects dehalogenation of alkyl halides to alkanes and radical addition of halides to alkenes, including dehalocyclizations: Org. Lett., 6, 4981 (2004).