CAS 1692-25-7 3-Pyridinylboronic acid - Materials / Alfa Chemistry

NAVIGATION

3-Pyridinylboronic acid

PRICE INQUIRY

Catalog Number

ACM1692257-1

CAS Number

1692-25-7

Product Name

3-Pyridinylboronic acid

Structure

Category

Salt

IUPAC Name

pyridin-3-ylboronic acid

Molecular Weight

122.92g/mol

Molecular Formula

C5H6BNO2;C5H6BNO2

Canonical SMILES

B(C1=CN=CC=C1)(O)O

InChI

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 is a versatile reagent primarily utilized in phosphine-free Suzuki-Miyaura cross-coupling reactions, offering a powerful tool for chemists engaged in forming carbon-carbon bonds. Its applications include regioselective coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation. Additionally, this reagent is valuable for N-arylation processes with a copper acetylacetonate catalyst and facilitates copper-mediated cyanation, as well as regioselective cyanation of electron-rich benzenes. Beyond these fundamental reactions, 3-pyridinylboronic acid plays a crucial role in synthesizing new linear poly(phenylpyridyl) chains through Suzuki coupling, and in the development of oligopyridyl foldamers that mimic the twist of alpha-helices. Importantly, it is also involved in creating a range of therapeutic agents, including significant enzymatic and kinase inhibitors, thereby making it indispensable in both medicinal chemistry and materials science.

Complexity

Covalently-Bonded Unit Count

Exact Mass

123.049159g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

3-pyridineboronic acid

Monoisotopic Mass

123.049159g/mol

Rotatable Bond Count

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