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179701 Aldrich

Triethylborane solution

1.0 M in THF

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Properties

Related Categories Boranes, Chemical Synthesis, Reduction, Synthetic Reagents
concentration   1.0 M in THF
density   0.865 g/mL at 25 °C

Description

Packaging

100, 800 mL in Sure/Seal™

Application

Catalyst for:
• Allylation of aldehydes1
• Decarboxylative C-C bond cleavage reactions2
• Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations3
• Regioselective hydroxyalkylation of unsaturated oxime ethers4

Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes5

Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential6

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Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
May form explosive peroxides.
Hazard Codes (Europe) 
F,C
Risk Statements (Europe) 
Safety Statements (Europe) 
16-26-36/37/39-45
RIDADR 
UN 3399BC 4.3(3) / PGII
WGK Germany 
1
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Reagents for C–C Bond Formation

Aldrich carries a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

Peer-Reviewed Papers

References

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1. S. Zhu, et al., Chem. Sci. 2, 1135-1140, (2011)

2. M. Kimura, et al., Heterocycles 82, 281-287, (2010)

3. Rhenium hydride/boron Lewis acid cocatalysis of alkene hydrogenations: activities comparable to those of precious metal systems. Y. Jiang, et al., J. Am. Chem. Soc. 132, 18233-18247, (2010)

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4. Aerobic hydroxylation of N-borylenamine: triethylborane-mediated hydroxyalkylation of alpha,beta-unsaturated oxime ether. M. Ueda, et al., Org. Lett. 11, 4632-4635, (2009)

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5. Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes. S. Ueng, et al., Org. Biomol. Chem. 9, 3415-3420, (2011)

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6. M. Pietrzak and B. Jedrzejewska, J. Organomet. Chem. 696, 2135-2141, (2011)

High performance of N-alkoxycarbonyl-imines in triethylborane-mediated tin-free radical addition. Yamada K, Konishi T, Nakano M, et al. J. Org. Chem. 77(3), 1547-53, (2012)

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Highly stereoselective synthesis of (2'R)-[2'-2H]-deoxyribonucleosides and synthesis of their oligonucleotides. Kawashima E, Sekine T, Miyahara M, et al. Nucleic Acids Symp. Ser. (27), 81-2, (1992)

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Rh-catalyzed reductive coupling reaction of aldehydes with conjugated dienes promoted by triethylborane. Kimura M, Nojiri D, Fukushima M, et al. Org. Lett. 11(17), 3794-7, (2009)

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Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane. Kimura M, Futamata M, Mukai R, et al. J. Am. Chem. Soc. 127(13), 4592-3, (2005)

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A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction. Paudyal MP, Rath NP, and Spilling CD Org. Lett. 12(13), 2954-7, (2010)

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Indenyl-functionalised triethylborane adduct of N-heterocyclic carbene: stepwise coordination of indenyl and NHC ligands toward molybdenum fragment. Takaki D, Okayama T, Shuto H, et al. Dalton Trans. 40(7), 1445-7, (2011)

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Macrocyclization by nickel-catalyzed, ester-promoted, epoxide-alkyne reductive coupling: total synthesis of (-)-gloeosporone. Trenkle JD and Jamison TF Angew. Chem. Int. Ed. Engl. 48(29), 5366-8, (2009)

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[Development of carbon radical addition to imine derivatives]. Miyabe H Yakugaku Zasshi 123(5), 285-94, (2003)

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Direct observation of the unstable intermediates in radical addition reaction by using an interfacing microchip combined with an NMR. Nakakoshi M, Ueda M, Sakurai S, et al. Magn. Reson. Chem. 45(11), 989-92, (2007)

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Stannyl radical addition-cyclization of oxime ethers connected with olefins. Miyabe H, Tanaka H, and Naito T Chem. Pharm. Bull. 52(1), 74-8, (2004)

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Diastereoselective solid-phase radical addition to oxime ether anchored to polymer support. Miyabe H, Konishi C, and Naito T Chem. Pharm. Bull. 51(5), 540-4, (2003)

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Solid-phase tandem radical addition-cyclization reaction: triethylborane-induced reaction of oxime ethers anchored to polymer support. Miyabe H, Tanaka H, and Naito T Chem. Pharm. Bull. 52(7), 842-7, (2004)

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Structure elucidation of the intermediate in triethylborane-mediated radical addition of oxime ethers with 2D- and 3D-DOSY NMR. Nakakoshi M, Ueda M, Sakurai S, et al. Magn. Reson. Chem. 44(8), 807-12, (2006)

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[Development of solid-phase radical reactions using oxime ethers as a radical acceptor]. Miyabe H Yakugaku Zasshi 120(8), 667-76, (2000)

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[Development of radical reactions in water aimed at environmentally benign synthetic reactions]. Ueda M Yakugaku Zasshi 124(6), 311-9, (2004)

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Merck 14,9668

Beil. 4,IV,4359

Fieser 9,482 / Fieser 10,416 / Fieser 17,366

Aldrich MSDS 1, 1750:B / Corp MSDS 1 (2), 3429:C / Corp MSDS 1 (2), 3429:D / Corp MSDS 1 (2), 3430:A / Corp MSDS 1 (2), 3430:B / RegBook 1 (2), 3021:C / Sax 6, 2639 / Structure Index 1, 477:C:9

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