CAS 617-86-7|硅烷 E3H|Triethylsilane|Triethylsilicon hydride|Silane E3H|triethylsilane|Triethylhydrosilane|NSC 93579|三乙基硅烷|triethylsilane|Triethyl silane

General Information

Structure

Molecular Formula

C₆H₁₆Si

Molecular Mass

116.27674

Exact Mass

116.10212704

Charge

InChI

InChI=1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3

InChIKey

AQRLNPVMDITEJU-UHFFFAOYSA-N

Canonic Smiles

CC[SiH](CC)CC

Isomeric Smiles

CC[SiH](CC)CC

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.153

LogD (pH = 7.4)

1.153

Log P

1.153

Molar Refractivity

31.8407

Polarizability

14.732455

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

硅烷 E3HTriethylsilaneTriethylsilicon hydrideSilane E3HNSC 93579Triethylhydrosilane三乙基硅烷Triethyl silane

IUPAC Traditional name

triethylsilane

IUPAC name

triethylsilane

Names and Identifiers

Registration numbers

MDL Number

MFCD00009018

CAS Number

617-86-7

Beilstein Number

1098278

PubChem SID

248892532485378124870410162228747

EC Number

210-535-3

PubChem CID

6327258

Registration numbers

Properties

Safety Information

Flammable (F)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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

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

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

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

Synonyms

硅烷 E3HTriethylsilaneTriethylsilicon hydrideSilane E3HNSC 93579Triethylhydrosilane三乙基硅烷Triethyl silane

IUPAC Traditional name

triethylsilane

IUPAC name

triethylsilane

Registration numbers

MDL Number

MFCD00009018

CAS Number

617-86-7

Beilstein Number

1098278

PubChem SID

248892532485378124870410162228747

EC Number

210-535-3

PubChem CID

6327258

Molecule Details

Sigma Aldrich

89706

230197

467448

90550

References

PubChem Literature

From Data Sources

• For use as a superior cation scavenger in peptide synthesis, see Triisopropylsilane, L09585.

• For reductive alkylation of indoles, see 2-Methylindole, A10764.

• For trans-hydrosilylation of alkynes, catalyzed by AlCl₃, see: J. Org. Chem., 61, 7354 (1996); 64, 2494 (1999).

• 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).

Bioactivity

PubChem BioAssay

Properties

Safety Information

Flammable (F)

Molecule

ID:134471