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179701

Sigma-Aldrich

Triethylborane solution

1.0 M in THF

Sinónimos:

Triethylboron

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About This Item

Fórmula lineal:
(C2H5)3B
Número de CAS:
97-94-9
Peso molecular:
97.99
Beilstein/REAXYS Number:
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.

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH019

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 1

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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)
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 tetramethylammonium phenyltrialkylborate salts by the addition of alkyllithium reagents to a triorganylborane or organoboranylhalides.
Pietrzak, Marek and J
Journal of Organometallic Chemistry, 696(10), 2135-2141 (2011)
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Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

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