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594377

Sigma-Aldrich

Triethylborane solution

2.0 M in diethyl ether

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About This Item

Linear Formula:
(C2H5)3B
CAS Number:
Molecular Weight:
97.99
Beilstein:
1731462
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:

reaction suitability

reagent type: reductant

concentration

2.0 M in diethyl ether

density

0.703 g/mL at 25 °C

SMILES string

CCB(CC)CC

InChI

1S/C6H15B/c1-4-7(5-2)6-3/h4-6H2,1-3H3

InChI key

LALRXNPLTWZJIJ-UHFFFAOYSA-N

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Application

Catalyst for:
  • Allylation of aldehydes
  • Decarboxylative C-C bond cleavage reactions
  • Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations
  • Regioselective hydroxyalkylation of unsaturated oxime ethers

Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes

Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1A - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

-40.0 °F

Flash Point(C)

-40 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hideto Miyabe et al.
Chemical & pharmaceutical bulletin, 51(5), 540-544 (2003-05-09)
Stereocontrol in radical reactions of oxime ether anchored to polymer support was studied. Highly diastereoselective solid-phase radical reaction was achieved by using triethylborane and diethylzinc as a radical initiator at low reaction temperature, providing a novel method for the synthesis
Masafumi Ueda
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 124(6), 311-319 (2004-06-01)
The aqueous medium radical reactions of a variety of imine derivatives such as oxime ether, oxime, hydrazone, nitrone, and N-sulfonylimine were investigated. Triethylborane-mediated intermolecular alkyl radical addition to glyoxylic oxime ether, oxime, and nitrone in water proceeded smoothly to give
Ken-ichi Yamada et al.
The Journal of organic chemistry, 77(3), 1547-1553 (2012-01-03)
Triethylborane-mediated tin-free radical alkylation of N-alkoxycarbonyl-imines, such as N-Boc-, N-Cbz-, and N-Teoc-imines, proceeded smoothly at a low temperature (-78 to -20 °C) to give the corresponding adducts in high yield. Although the formation of isocyanate was the major unfavorable reaction
Hideto Miyabe et al.
Chemical & pharmaceutical bulletin, 52(1), 74-78 (2004-01-08)
Stannyl radical addition-cyclization of oxime ethers connected with olefin moieties was studied. The radical reactions proceeded effectively by the use of triethylborane as a radical initiator to provide the functionalized pyrrolidines via a carbon-carbon bond-forming process.
Hideto Miyabe
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 123(5), 285-294 (2003-05-30)
This review summarizes the new carbon-carbon bond construction methods based on the radical reaction of imine derivatives. The intermolecular carbon radical addition to oxime ethers proceeded smoothly in the presence of BF3.OEt2. A high degree of stereocontrol in the reaction

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