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195030

Sigma-Aldrich

Triethylborane solution

1.0 M in hexanes

Synonym(s):

Triethylboron

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About This Item

Linear Formula:
(C2H5)3B
CAS Number:
97-94-9
Molecular Weight:
97.99
Beilstein:
1731462
MDL number:
MFCD00009022
UNSPSC Code:
12352001
PubChem Substance ID:
24851669
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: reductant

concentration

1.0 M in hexanes

density

0.675 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 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)

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Nervous system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-32.8 °F

Flash Point(C)

-36 °C

Certificates of Analysis (COA)

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Sigma-Aldrich

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Free-radical reaction of imine derivatives in water.
Miyabe H, et al.
The Journal of Organic Chemistry, 65(16), 5043-5047 (2000)
Synthesis of poly (2-substituted-1-propenylene)s from allylic arsonium ylides.
Mondiere R, et al.
Macromolecules, 38(3), 663-668 (2005)
E Kawashima et al.
Nucleic acids symposium series, (27)(27), 81-82 (1992-01-01)
Highly stereoselective synthesis of (2'R)-[2'-2H]-2'-deoxyribonucleosides (2'R:2'S = > 99:1) were accomplished by treating 2'-bromo-3',5'-O-TPDS-2'-deoxyribonucleosides with tributyltin deuteride at lower temperatures such as -60 degrees C in the presence of triethylborane. Moreover, synthesis of some oligodeoxyribonucleosides involving them will be described.
Masanari Kimura et al.
Journal of the American Chemical Society, 127(13), 4592-4593 (2005-03-31)
Under palladium catalysis, Et3B nicely promotes allyl alcohols to undergo C3-selective allylation of indoles and tryptophan; the yields range 75-95%.
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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