512125

3-Pyridinylboronic acid

≥95.0%

• Synonym(s): 3-Pyridineboronic acid, 3-Pyridylboronic acid, Dihydroxy(3-pyridyl)borane, Pyridin-3-ylboronic acid
• 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

Properties

• 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

Description

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

Safety Information

• 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)