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Sigma-Aldrich

Triethylborane

≥95%

Synonym(s):

Triethylboron

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About This Item

Linear Formula:
(C2H5)3B
CAS Number:
97-94-9
Molecular Weight:
97.99
EC Number:
202-620-9
MDL number:
MFCD00009022
UNSPSC Code:
12352001
PubChem Substance ID:
24855572
NACRES:
NA.22

Quality Level

100

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

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Certificates of Analysis (COA)

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Tetrahedron, 49, 7193-7193 (1993)
A Convenient Preparation of Trimethylborane and Triethylborane
Koster, R, et al.
Synth. React. Inorg. Met.-Org. Chem. , 3(4), 359-367 (1973)
Aldrichimica Acta, 6, 21-21 (1973)
Triethylborane-mediated atom transfer radical cyclization reaction in water
Yorimitsu H, et al.
The Journal of Organic Chemistry, 63(23), 8604-8605 (1998)
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
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Reagents for C–C Bond Formation

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