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512125

Sigma-Aldrich

3-Pyridinylboronic acid

≥95.0%

Synonyme(s) :

3-Pyridineboronic acid, 3-Pyridylboronic acid, Dihydroxy(3-pyridyl)borane, Pyridin-3-ylboronic acid

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About This Item

Formule empirique (notation de Hill):
C5H6BNO2
Numéro CAS:
1692-25-7
Poids moléculaire :
122.92
Numéro MDL:
MFCD00674177
Code UNSPSC :
12352103
ID de substance PubChem :
24873612
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

≥95.0%

Forme

solid

Pf

>300 °C (lit.)

Chaîne SMILES 

OB(O)c1cccnc1

InChI

1S/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H

Clé InChI

ABMYEXAYWZJVOV-UHFFFAOYSA-N

Catégories apparentées

Application

3-Pyridinylboronic acid can be used as a reagent for:
  • Phosphine-free Suzuki-Miyaura cross-coupling reactions.
  • Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation.
  • N-arylation using copper acetylacetonate catalyst.
  • Copper-mediated cyanation and regioselective cyanation of electron-rich benzenes.

It can also be used to prepare:
  • New linear poly(phenylpyridyl) chains by Suzuki coupling.
  • Oligopyridyl foldamers as mimics of a-helix twist.
  • Many highly significant therapeutic enzymatic and kinase inhibitors and receptor antagonists.
  • Pyridine substituted pyridinium N-(2′-azinyl)aminides by reacting with dibromo pyridinium aminides via Suzuki coupling reaction.

Autres remarques

Contains varying amounts of anhydride

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
MKCQ2668
MKBZ3819V
MKBW4557V
MKBR3950V
MKBD4313V

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Sigma-Aldrich

436836

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5-Chloro-3-pyridineboronic acid ≥95%

Sigma-Aldrich

721034

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3-Furanylboronic acid ≥95.0%

Sigma-Aldrich

512168

3-Furanylboronic acid

Jana Sopkova-de Oliveira Santos et al.
Journal of chemical information and modeling, 52(2), 429-439 (2011-12-27)
Protein-protein interactions are central to many biological processes, from intracellular communication to cytoskeleton assembly, and therefore represent an important class of targets for new therapeutics. The most common secondary structure in natural proteins is an α-helix. Small molecules seem to
Tetrahedron Letters, 47, 6457-6457 (2006)
Brian C Shook et al.
Journal of medicinal chemistry, 55(3), 1402-1417 (2012-01-14)
The design and characterization of two, dual adenosine A(2A)/A(1) receptor antagonists in several animal models of Parkinson's disease is described. Compound 1 was previously reported as a potential treatment for Parkinson's disease. Further characterization of 1 revealed that it was
Justin I Montgomery et al.
Journal of medicinal chemistry, 55(4), 1662-1670 (2012-01-20)
The synthesis and biological activity of a new series of LpxC inhibitors represented by pyridone methylsulfone hydroxamate 2a is presented. Members of this series have improved solubility and free fraction when compared to compounds in the previously described biphenyl methylsulfone
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This brochure contains a comprehensive selection of boronic acids, boronic acid esters, diboron esters, and transition-metal catalysts useful for the Suzuki–Miyaura coupling reaction

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The Suzuki-Miyaura cross-coupling reaction is an important and extensively used reaction in organic chemistry with applications in polymer science and in the fine chemicals and pharmaceutical industries.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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