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About This Item
Linear Formula:
(C2H5)3B
CAS Number:
Molecular Weight:
97.99
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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:
Catalyst for:
Modifier for single-site organochromium ethylene polymerization catalysts
- 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:
Compatible with the following:
- Aldrich® Sure/Pac™ station for liquefied gases Z566446
- PTFE Sealing tape Z104388 or Z221880
- Straight septum-inlet adapter Z118141 with septa Z565687 or Z565695
Legal Information
Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC
also commonly purchased with this product
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Description
Pricing
recommended
Product No.
Description
Pricing
septum inlet adapter
Product No.
Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary 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
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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)
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
Triethylborane-mediated atom transfer radical cyclization reaction in water
Yorimitsu H, et al.
The Journal of Organic Chemistry, 63(23), 8604-8605 (1998)
Aldrichimica Acta, 6, 21-21 (1973)
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