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195030

Sigma-Aldrich

Triethylborane solution

1.0 M in hexanes

Sinônimo(s):

Triethylboron

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About This Item

Fórmula linear:
(C2H5)3B
Número CAS:
97-94-9
Peso molecular:
97.99
Beilstein:
1731462
Número MDL:
MFCD00009022
Código UNSPSC:
12352001
ID de substância PubChem:
24851669
NACRES:
NA.22

Formulário

liquid

adequação da reação

reagent type: reductant

concentração

1.0 M in hexanes

densidade

0.675 g/mL at 25 °C

cadeia de caracteres SMILES

CCB(CC)CC

InChI

1S/C6H15B/c1-4-7(5-2)6-3/h4-6H2,1-3H3

chave InChI

LALRXNPLTWZJIJ-UHFFFAOYSA-N

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Aplicação

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)

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Central nervous system, Nervous system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

-32.8 °F

Ponto de fulgor (°C)

-36 °C

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Certificados de análise (COA)

Lot/Batch Number
SHBK6670
43096KJ
08429KH
00130HH
08330AH

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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)
Hideto Miyabe et al.
Chemical & pharmaceutical bulletin, 51(5), 540-544 (2003-05-09)
Stereocontrol in radical reactions of oxime ether anchored to polymer support was studied. Highly diastereoselective solid-phase radical reaction was achieved by using triethylborane and diethylzinc as a radical initiator at low reaction temperature, providing a novel method for the synthesis
Masafumi Ueda
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 124(6), 311-319 (2004-06-01)
The aqueous medium radical reactions of a variety of imine derivatives such as oxime ether, oxime, hydrazone, nitrone, and N-sulfonylimine were investigated. Triethylborane-mediated intermolecular alkyl radical addition to glyoxylic oxime ether, oxime, and nitrone in water proceeded smoothly to give
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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