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195030

Sigma-Aldrich

Triethylborane solution

1.0 M in hexanes

Synonym(s):

Triethylboron

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About This Item

Linear Formula:
(C2H5)3B
CAS Number:
97-94-9
Molecular Weight:
97.99
Beilstein:
1731462
MDL number:
MFCD00009022
UNSPSC Code:
12352001
PubChem Substance ID:
24851669
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: reductant

concentration

1.0 M in hexanes

density

0.675 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
Triethylborane can be used:
  • As a radical initiator and terminator of free-radical reactions in aqueous media.(1)
  • To synthesize polymers such as poly(2-substituted-1-propenylene)s by reacting with 2-substituted allylic arsonium ylides.(2)

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1A - STOT RE 1 Inhalation - STOT SE 3

Target Organs

Central nervous system, Nervous system

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

-32.8 °F

Flash Point(C)

-36 °C

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Certificates of Analysis (COA)

Lot/Batch Number
0000423638
0000423638
0000419207
0000419207
0000251712

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Synthesis of poly (2-substituted-1-propenylene)s from allylic arsonium ylides.
Mondiere R, et al.
Macromolecules, 38(3), 663-668 (2005)
Free-radical reaction of imine derivatives in water.
Miyabe H, et al.
The Journal of Organic Chemistry, 65(16), 5043-5047 (2000)
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
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