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637998

Sigma-Aldrich

Vinylboronic anhydride pyridine complex

95%

Synonyme(s) :

2,4,6-Trivinylcyclotriboroxane pyridine complex, Trivinyl-boroxin pyridine complex, Trivinylcyclotriboroxane pyridine complex

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About This Item

Formule empirique (notation de Hill):
C6H9B3O3 · C5H5N
Numéro CAS:
442850-89-7
Poids moléculaire :
240.67
Numéro MDL:
MFCD03839940
Code UNSPSC :
12352103
ID de substance PubChem :
24882902
Nomenclature NACRES :
NA.22

Pureté

95%

Forme

solid

Température de stockage

−20°C

Chaîne SMILES 

c1ccncc1.C=Cb2ob(C=C)ob(C=C)o2

InChI

1S/C6H9B3O3.C5H5N/c1-4-7-10-8(5-2)12-9(6-3)11-7;1-2-4-6-5-3-1/h4-6H,1-3H2;1-5H

Clé InChI

YLHJACXHRQQNQR-UHFFFAOYSA-N

Application

Reagent used for
  • Suzuki-Miyaura cross-coupling
  • Stereoselective synthesis via Palladium-catalyzed carboamination
  • Alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking 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
  • Kinetic resolution of phosphoryl and sulfonyl esters of binaphthol derivatives via Pd-catalyzed alcoholysis of their vinyl ethers
  • Stereoselective isomerization of N-allyl aziridines into Z-enamines by using rhodium hydride catalysis
  • Kinetic resolution of axially chiral biaryl derivatives via palladium/chiral diamine ligand-catalyzed alcoholysis
  • Transition metal-catalyzed alkenylation of aziridines, cycloaddition and thermal rearrangement reactions
  • Intramolecular Heck reaction strategy for synthesis of functionalized tetrahydroanthracenes

Reagent used for Preparation of
  • BACE-1 inhibitors and SAR of cyclic sulfone hydroxyethylamines
  • Distorted spiropentanes
  • Small molecule bradykinin B2 receptor antagonists in angioedema therapy
  • Enol Ethers
  • Styryl cyclobutanone

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Conseils de prudence

P305 + P351 + P338

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

176.0 °F - closed cup

Point d'éclair (°C)

80 °C - closed cup

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Consulter la Bibliothèque de documents

Hiroshi Aoyama et al.
Journal of the American Chemical Society, 127(30), 10474-10475 (2005-07-28)
Palladium-diamine complexes catalyzed kinetic resolution of axially chiral 2,2'-dihydroxy-1,1'-biaryls by alcoholysis of vinyl ethers. The reaction proceeded with high selectivity for various kinds of biaryls. This process is applicable to not only binaphthols but also biphenols, which have been considered
Yosuke Taniguchi et al.
Bioorganic & medicinal chemistry, 18(8), 2894-2901 (2010-03-30)
We have previously reported that the 2-amino-6-vinylpurine (AVP) nucleoside exhibits a highly efficient and selective crosslinking reaction toward cytosine and displayed an improved antisense inhibition in cultured cells. In this study, we further investigated the alkyl-connected AVP nucleoside analogs for
Kinetic resolution of phosphoryl and sulfonyl esters of 1,1'-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers
Sakuma, T.; et al.
Tetrahedron, 19, 1593-1599 (2008)
Intramolecular Heck reaction strategy for the synthesis of functionalized tetrahydroanthracenes: a facile formal total synthesis of the linear abietane diterpene, umbrosone
Sengupta, S.; et al.
Tetrahedron Letters, 46, 1515-1519 (2005)
Derek S Tsang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(3), 886-894 (2007-11-10)
In the presence of rhodium(I) hydride catalysts, tertiary N-allylamines are known to isomerise into E enamines. In contrast, we have recently found that N-allylaziridines isomerise to form Z enamines. On the basis of literature data, the most likely mechanism of
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