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179701

Sigma-Aldrich

Triethylborane solution

1.0 M in THF

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
eCl@ss:
38120201
PubChem Substance ID:
24850826
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

density

0.865 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 is used as a 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


It can be employed as a reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes and for the synthesis of tetramethylammonium trialkylphenylborate salts.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ8068
SHBJ6115
SHBJ0623
SHBH2155V
SHBD9512V

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Aerobic Hydroxylation of N-Borylenamine: Triethylborane-Mediated Hydroxyalkylation of α, β-Unsaturated Oxime Ether.
Ueda M, et al.
Organic Letters, 11(20), 4632-4635 (2009)
Highly enantioselective palladium-catalyzed umpolung allylation of aldehydes.
Zhu, Shou-Fei and Qiao, Xiang-Chen and Zhang, Yong-Zhen and Wang, Li-Xin and Zhou, Qi-Lin
Chemical Science, 2(6), 1135-1140 (2011)
Rhenium hydride/boron Lewis acid cocatalysis of alkene hydrogenations: Activities comparable to those of precious metal systems.
Jiang, Yanfeng and Hess, Jeannine and Fox, Thomas and Berke, Heinz
Journal of the American Chemical Society, 132(51), 18233-18247 (2010)
Synthesis of N-heterocyclic carbene boranes via silver N-heterocyclic carbene complexes.
Ono S, et al.
Polyhedron, 137(20), 296-305 (2017)
Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides.
Alexander, Juliana R and Cook, Matthew J
Organic Letters, 19(21), 5822-5825 (2017)
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