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512125

Sigma-Aldrich

3-Pyridinylboronic acid

≥95.0%

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C5H6BNO2
Číslo CAS:
1692-25-7
Molekulová hmotnost:
122.92
MDL number:
MFCD00674177
UNSPSC Code:
12352103
PubChem Substance ID:
24873612
NACRES:
NA.22

assay

≥95.0%

form

solid

mp

>300 °C (lit.)

SMILES string

OB(O)c1cccnc1

InChI

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

InChI key

ABMYEXAYWZJVOV-UHFFFAOYSA-N

Související kategorie

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.

Other Notes

Contains varying amounts of anhydride

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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2-Thienylboronic acid ≥95.0%

Sigma-Aldrich

436836

2-Thienylboronic acid

5-Chloro-3-pyridineboronic acid ≥95%

Sigma-Aldrich

721034

5-Chloro-3-pyridineboronic acid

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
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
Synthesis of new linear poly(phenylpyridyl) chains
Perato, S.; et al.
Tetrahedron, 68, 1910-1917 (2012)
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
Regioselective Suzuki coupling on pyridinium N-(3,5-dibromoheteroar-2-yl)aminides
M. Jose R, et al.
Tetrahedron Letters, 47, 36, 6457-6460 (2006)
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Sortimentní položky

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

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