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195030
Triethylborane solution
1.0 M in hexanes
Synonym(s):
Triethylboron
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About This Item
Linear Formula:
(C2H5)3B
CAS Number:
Molecular Weight:
97.99
Beilstein:
1731462
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22
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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:
Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes
Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential
- 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 Statements
Precautionary Statements
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
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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.
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
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
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