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467448

Sigma-Aldrich

Triethylsilane

97%

Synonym(s):

NSC 93579, Triethylhydrosilane, Triethylsilicon hydride

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About This Item

Linear Formula:
(C2H5)3SiH
CAS Number:
617-86-7
Molecular Weight:
116.28
Beilstein/REAXYS Number:
1098278
EC Number:
210-535-3
MDL number:
MFCD00009018
UNSPSC Code:
12352103
PubChem Substance ID:
24870410
NACRES:
NA.22

Quality Level

200

assay

97%

reaction suitability

reagent type: reductant

refractive index

n20/D 1.412 (lit.)

bp

107-108 °C (lit.)

density

0.728 g/mL at 25 °C (lit.)

SMILES string

CC[SiH](CC)CC

InChI

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

InChI key

AQRLNPVMDITEJU-UHFFFAOYSA-N

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Application

Catalyst for:
  • Synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain
  • Redox initiated cationic polymerization
  • Beckmann rearrangement of cyclododecanone oxime
  • Regioselective reductive coupling of enones and allenes

Catalyst reactivation after catalyst polymerization of styrene

Studies involving the prediction of organosilicon flash points
Triethylsilane can be used as:
  • A reducing agent in the regioselective reductive coupling of enones and allenes.
  • A reagent in the redox initiated cationic polymerization.
  • A reagent in catalytic transfer hydrogenation, reduction of alkyl halides and silylation of aromatic C-H bonds, etc.
  • As a reagent for the generation of indium hydride (Cl2InH) applicable as a catalyst for the intramolecular cyclization of enynes.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

21.2 °F

flash_point_c

-6 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Triethylsilane- Indium (III) Chloride System as a Radical Reagent.
Hayashi N, et al.
Organic Letters, 6(26), 4981-4983 (2004)
Pd- C-induced catalytic transfer hydrogenation with triethylsilane.
Mandal PK and McMurray JS
The Journal of Organic Chemistry, 72(17), 6599-6601 (2007)
Iridium-catalyzed reduction of alkyl halides by triethylsilane.
Yang J and Brookhart M
Journal of the American Chemical Society, 129(42), 12656-12657 (2007)
Regioselective Nickel-Catalyzed Reductive Couplings of Enones and Allenes.
Li W, et al.
Angewandte Chemie (International Edition in English), 49(46), 8712-8716 (2010)
Redox-Initiated Cationic Polymerization: Reduction of Dialkylphenacylsulfonium Salts by Silanes.
Molleo M and Crivello JV
Macromolecules, 42(12), 3982-3991 (2009)
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