Substance
ID:714166
Names and Identifiers
Synonyms
Triethylsilane三乙基硅烷
IUPAC Traditional name
triethylsilane
IUPAC name
triethylsilane
Registration numbers
Beilstein Number
CAS Number
EC Number
MDL Number
Properties
Safety Information
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
Flammable gases, category 1
Flammable aerosols, categories 1,2
Flammable liquids, categories 1,2,3
Self-reactive substances and mixtures, Types B,C,D,E,F
Pyrophoric liquids, category 1
Pyrophoric solids, category 1
Self-heating substances and mixtures
Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3
Organic peroxides, Types B,C,D,E,F
Packing Group
II
Risk Statements
11-36/37/38
GHS Precautionary statements
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
UN Number
UN1993
Safety Statements
9-16-26-33-37-60
Storage Warning
Moisture Sensitive
Hazard Class
3
TSCA Listed
是
European Hazard Symbols
Irritant (Xi)
Flammable (F)GHS Hazard statements
H225-H315-H319-H335
Physical Property
Melting Point
-157°C
Density
0.728
Refractive Index
1.4120
Boiling Point
107-108°C
Flash Point
-6°C(21°F)
Product Information
Purity
98+%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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.
• For use as a superior cation scavenger in peptide synthesis, see Triisopropylsilane, L09585.
• 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):
• 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).
• 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).
• For reductive alkylation of indoles, see 2-Methylindole, A10764.
• 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).
• 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).
• For trans-hydrosilylation of alkynes, catalyzed by AlCl3, see: J. Org. Chem., 61, 7354 (1996); 64, 2494 (1999).
• 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).
• Aryl halides have been silylated using PtO2 as a catalyst, to give aryltriethylsilanes: Org. Let.., 8, 931 (2006).
• 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).