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H28703 Vinylboronic anhydride pyridine complex, 95%

Número CAS
95010-17-6
Nombre Alternativo
O'Shea's reagent
Trivinylboroxin pyridine complex

Stock No. Tamaño Precio ($) Cantidad Disponibilidad
H28703-03 1g 51,90
H28703-06 5g 160,00
H28703-14 25g 697,00
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Vinylboronic anhydride pyridine complex, 95%

MDL
MFCD03839940

Propiedades químicas

Fórmula
C6H9B3O3
Peso molecular
161.57
Punto de fusión
44-52°
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Store under Nitrogen.
Solubilidad
Soluble in methanol.

Aplicaciones

Reagent used for Suzuki-Miyaura cross-coupling, stereoselective synthesis via Palladium-catalyzed carboamination, Alkyl-connected 2-amino-6-vinylpurine (AVP) cross linking agent to cytosine base in RNA, Kaiser oxime resin-derived palladacycle as a recoverable polymeric precatalyst in Suzuki-Miyaura cross-coupling reactions in aqueous media and Kinetic resolution of phosphoryl and sulfonyl esters of binaphthol derivatives via Pd-catalyzed alcoholysis of their vinyl ethers.

Notas

Moisture Sensitive, store away from water/moisture. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store under dry inert gas.

Referencias documentales

Kuan-Jen Su; Jean-Luc Mieusset; Vladimir B Arion; Wolfgang Knoll; Lothar Brecker; Udo H Brinker. Efforts toward distorted spiropentanes. Journal of Organic Chemistry. 2010, 75(21), 7494-7497.

Amanda F Ward; and John P Wolfe. Stereoselective synthesis of substituted 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols.Organic Letters. 2011, 13(17), 4728-4731.

Stable equivalent of the readily-polymerizable vinylboronic acid, first reported by Matteson: J. Org. Chem., 27, 3712 (1962), and more recently adopted by O'Shea as a vinylboron unit for Suzuki cross-coupling reactions with aryl halides to give substituted styrenes: J. Org. Chem., 67, 4968 (2002). The reaction has been applied to the formation of ortho-Boc-amino styrenes, further reaction of which has been developed as a route to diversely functionalized indoles: J. Am. Chem. Soc., 125, 4054 (2003). Copper(II) acetate mediated coupling with phenols affords an efficient synthesis of aryl vinyl ethers: J. Org. Chem., 69, 5087 (2004).

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Indicaciones de precaución: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Código de tarifa arancelaria unificado
2933.39
TSCA
No

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