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512125

Sigma-Aldrich

3-Pyridinylboronic acid

≥95.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H6BNO2
CAS Number:
1692-25-7
Molecular Weight:
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

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Cu(acac)2-catalyzed N-arylations of phenylurea with arylboronic acid
Gavade, S.; et al.
Synthetic Communications, 42, 1704-1714 (2012)
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Articles

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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