Search
Element Search
Structure Search
Thermo Scientific™
Vinylboronic anhydride pyridine complex, 95%
CAS: 95010-17-6 | C11H14B3NO3 | 240.667 g/mol
Have Questions?
Change view
Catalog number H28703.06
also known as H28703-06
Price (USD)
359.65
Online Exclusive
399.00Save 39.35 (10%)
Each
Quantity:
5 g
Price (USD)
359.65
Online Exclusive
399.00Save 39.35 (10%)
Each
Chemical Identifiers
CAS95010-17-6
IUPAC Namepyridine; triethenyl-1,3,5,2,4,6-trioxatriborinane
Molecular FormulaC11H14B3NO3
InChI KeyYLHJACXHRQQNQR-UHFFFAOYSA-N
SMILESC1=CC=NC=C1.C=CB1OB(OB(O1)C=C)C=C
View more
Specifications
Specification Sheet
Specification SheetAssay by NMR>94.0%
Appearance (Color)White to cream or pale yellow
Proton NMRConforms to structure
FormCrystalline powder
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in methanol.
Notes
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.
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.
Solubility
Soluble in methanol.
Notes
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.
RUO – Research Use Only
General References:
- 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).