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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:
97-94-9
Molecular Weight:
97.99
Beilstein/REAXYS Number:
1731462
MDL number:
MFCD00009022
UNSPSC Code:
12352001
PubChem Substance ID:
24881503

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

signalword

Danger

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

supp_hazards

EUH019

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 1

flash_point_f

-40.0 °F

flash_point_c

-40 °C

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH1393V
SHBC4334V
25796BM
15224KH
16320BB

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H Miyabe
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 120(8), 667-676 (2000-08-18)
Triethylborane has the potential to induce radical reactions on solid support and the solid-phase radical reactions were achieved by using triethylborane as a radical initiator. The intermolecular carbon radical addition to glyoxylic oxime ether anchored to Wang resin proceeded under
Masamichi Nakakoshi et al.
Magnetic resonance in chemistry : MRC, 44(8), 807-812 (2006-05-27)
The structures of the components in the triethylborane-mediated radical addition reaction of oxime ether were investigated by 1H- and 3D-DOSY NMR methods. It has been impossible to physically separate the unstable intermediates; therefore, the structures were thus far unidentified. It
Hideto Miyabe et al.
Chemical & pharmaceutical bulletin, 52(7), 842-847 (2004-07-17)
Tandem radical addition-cyclization of oxime ethers anchored to polymer support was studied. The reaction of oxime ethers with stannyl radical proceeded effectively by the use of triethylborane as a radical initiator. The alkyl radical addition-cyclization reactions of oxime ether connected
Daichi Takaki et al.
Dalton transactions (Cambridge, England : 2003), 40(7), 1445-1447 (2011-01-15)
Indenyl-functionalised BEt(3)-adduct NHCs were prepared by the reaction of imidazolium pro-ligands with LiBEt(3)H. This compound was converted into the indenyl-coordinate molybdenum complex dangling the NHC·BEt(3) moiety as a substituent. The stepwise coordination of NHC afforded a chelate-type mononuclear complex as
Masamichi Nakakoshi et al.
Magnetic resonance in chemistry : MRC, 45(11), 989-992 (2007-10-10)
Direct observation of the unstable intermediate in the radical addition reaction of the oxime ether 1 mediated by triethylborane (Et(3)B) is described using (1)H and (11)B micro channeled cell for synthesis monitoring (MICCS), which was recently developed as an interfacing
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