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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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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
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
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
Masanari Kimura et al.
Organic letters, 11(17), 3794-3797 (2009-08-12)
Rh(I) catalyzes the reductive coupling reaction of a wide variety of aldehydes with conjugated dienes in the presence of a stoichiometric amount of triethylborane to provide homoallyl alcohols in a single operation.
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
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