triethylsilane

• ChemBase ID: 134471
• Molecular Formular: C6H16Si
• Molecular Mass: 116.27674
• Monoisotopic Mass: 116.10212704
• SMILES: CC[SiH](CC)CC
• Canonical SMILES: CC[SiH](CC)CC
• InChI: InChI=1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3
• InChIKey: AQRLNPVMDITEJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triethylsilane
• IUPAC Traditional name: triethylsilane
• Synonyms: Triethyl silane; NSC 93579; Triethylhydrosilane; Triethylsilicon hydride; Silane E3H; Triethylsilane; 硅烷 E3H; 三乙基硅烷

Database IDs

• CAS Number: 617-86-7
• EC Number: 210-535-3
• MDL Number: MFCD00009018
• Beilstein Number: 1098278
• PubChem SID: 24870410; 24853781; 24889253; 162228747
• PubChem CID: 6327258

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.153
• LogD (pH = 7.4): 1.153
• Log P: 1.153
• Molar Refractivity: 31.8407 cm^3
• Polarizability: 14.732455 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -157°C
• Boiling Point: 107-108 °C(lit.); 107-108°C
• Flash Point: 26.6 °F; -3 °C; -6°C(21°F)
• Density: 0.728; 0.728 g/mL at 25 °C(lit.)
• Refractive Index: 1.4120; n20/D 1.412; n20/D 1.412(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-36/37/38; 11-52/53
• Safety Statements: 9-16-26-33-37-60; 9-16-29-33-61
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H315-H319-H335; H225-H412
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P273
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2

Product Information

• Purity: ≥97.0% (GC); ≥98.0% (GC); 97%; 98+%; 99%
• Grade: produced by Wacker; purum
• Linear Formula: (C2H5)3SiH

DETAILS

Sigma Aldrich - 467448

Packaging
25, 100 mL in Sure/Seal™
Application
Catalyst for:
• Synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain1
• Redox initiated cationic polymerization2,3
• Beckmann rearrangement of cyclododecanone oxime4
• Regioselective reductive coupling of enones and allenes5Catalyst reactivation after catalyst polymerization of styrene6Studies involving the prediction of organosilicon flash points7

Sigma Aldrich - 230197

Application
Used in a study of the reduction of 2-chromanols; syn-selectivity observed with TES.8
Versatile reducing agent
Catalyst for:
• Synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain1
• Redox initiated cationic polymerization2,3
• Beckmann rearrangement of cyclododecanone oxime4
• Regioselective reductive coupling of enones and allenes5Catalyst reactivation after catalyst polymerization of styrene6Studies involving the prediction of organosilicon flash points7
Packaging
25, 100 g in Sure/Seal™
5 g in glass bottle

Sigma Aldrich - 89706

Other Notes
Silane E3H
prices for bulk quantities on request
Application
Catalyst for:
• Synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain1
• Redox initiated cationic polymerization2,3
• Beckmann rearrangement of cyclododecanone oxime4
• Regioselective reductive coupling of enones and allenes5Catalyst reactivation after catalyst polymerization of styrene6Studies involving the prediction of organosilicon flash points7

Sigma Aldrich - 90550

Other Notes
Reagent for the reduction of various functional groups (e.g. acyl halides to aldehydes, alkyl halides and secondary alcohols to hydrocarbons), review8,9,10; Silylating agent for alcohols, phenols, etc.11,12
Application
Catalyst for:
• Synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain1
• Redox initiated cationic polymerization2,3
• Beckmann rearrangement of cyclododecanone oxime4
• Regioselective reductive coupling of enones and allenes5Catalyst reactivation after catalyst polymerization of styrene6Studies involving the prediction of organosilicon flash points7

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).