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Merck

257192

Sigma-Aldrich

Triethylborane

≥95%

Sinónimos:

Triethylboron

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About This Item

Fórmula lineal:
(C2H5)3B
Número de CAS:
Peso molecular:
97.99
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

assay

≥95%

reaction suitability

reagent type: reductant

refractive index

n20/D 1.397 (lit.)

bp

95 °C (lit.)

mp

−93 °C (lit.)

density

0.677 g/mL at 25 °C (lit.)

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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General description

Triethylborane (Et3B) is an organoborane pyrophoric liquid. It is prepared on the plant scale by the reaction of AlEt3 and KBF4. Et3B is widely used as a precursor for the preparation of reducing agents such as lithium triethylborohydride and sodium triethylborohydride. It can also be utilized as an initiator in radical cyclization reactions.

Application

Reagent for:
  • Enantioselective umpolung allylation of aldehydes
  • Preparation of tetramethylammonium trialkylphenylborate salts

Catalyst for:
  • Radical reductions of alkyl bromides and iodides bearing electron withdrawing groups with N-heterocyclic carbene boranes
  • Synthesis of 1-substituted pyrrolines by N-diallylation of amines and ring-closing metathesis
  • Decarboxylative C-C bond cleavage reactions
  • Alkene hydrogenations
  • Aminyl radical cyclizations onto silyl enol ethers

Modifier for single-site organochromium ethylene polymerization catalysts
Used with lithium tri-tert-butoxyaluminohydride (cat. no. L2904) in the reductive cleavage of ethers and epoxides. Used in the deoxygenation of primary and secondary alcohols.

Packaging

Supplied in a Sure/Pac cylinder and has a 1/4-turn bronze ball valve with a female 1/4" NPT outlet thread (Z122661) installed. Before using the cylinder, ensure that the valve is closed, then remove carbon steel plug that seals the outlet valve.

Compatible with the following:For instructions please refer to technical bulletin AL-136: The Aldrich Sure/Pac Cylinder System

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

Optional

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also commonly purchased with this product

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septum inlet adapter

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signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 1

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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Triethylborane-mediated atom transfer radical cyclization reaction in water
Yorimitsu H, et al.
The Journal of Organic Chemistry, 63(23), 8604-8605 (1998)
Aldrichimica Acta, 6, 21-21 (1973)
A Convenient Preparation of Trimethylborane and Triethylborane
Koster, R, et al.
Synth. React. Inorg. Met.-Org. Chem. , 3(4), 359-367 (1973)
Masafumi Ueda et al.
Organic letters, 11(20), 4632-4635 (2009-10-09)
Intermolecular hydroxyalkylation of alpha,beta-unsaturated imines involving Et3B-mediated regioselective alkyl radical addition and subsequent hydroxylation with molecular oxygen has been developed, in which N-borylenamine generated by trapping of the enaminyl radical with Et3B was a key intermediate in the proposed aerobic
Tetrahedron, 49, 7193-7193 (1993)

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