512125
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:
Molecular Weight:
122.92
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Quality Level
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
Application
3-Pyridinylboronic acid can be used as a reagent for:
It can also be used to prepare:
- 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
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
Synthesis of new linear poly(phenylpyridyl) chains
Perato, S.; et al.
Tetrahedron, 68, 1910-1917 (2012)