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257192

Sigma-Aldrich

Triethylborane

≥95%

Synonym(s):
Triethylboron
Linear Formula:
(C2H5)3B
CAS Number:
Molecular Weight:
97.99
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

100 g in Sure-Pac™

Recommended products

Angled septum-inlet adapter Z118206 or straight septum-inlet adapter, 6mm I.D. inlet, Z118141 or straight septum-inlet adapter, 13mm I.D. inlet, Z118192 is recommended.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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