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Merck
CN

594377

Triethylborane solution

2.0 M in diethyl ether

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About This Item

Linear Formula:
(C2H5)3B
CAS Number:
97-94-9
Molecular Weight:
97.99
PubChem Substance ID:
24881503
UNSPSC Code:
12352001
Beilstein/REAXYS Number:
1731462
MDL number:
MFCD00009022

Key Documents

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SMILES string

CCB(CC)CC

InChI

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

InChI key

LALRXNPLTWZJIJ-UHFFFAOYSA-N

reaction suitability

reagent type: reductant

concentration

2.0 M in diethyl ether

density

0.703 g/mL at 25 °C

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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

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1A - STOT SE 3

target_organs

Central nervous system

supp_hazards

EUH019

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

WGK 1

flash_point_f

-40.0 °F

flash_point_c

-40 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH1393V
SHBC4334V
25796BM
15224KH
16320BB

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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%.
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
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.
Mahesh P Paudyal et al.
Organic letters, 12(13), 2954-2957 (2010-06-10)
Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent
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
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