(pyridin-3-yl)boronic acid

• ChemBase ID: 7339
• Molecular Formular: C5H6BNO2
• Molecular Mass: 122.91764
• Monoisotopic Mass: 123.04915884
• SMILES: c1cncc(c1)B(O)O
• Canonical SMILES: OB(c1cccnc1)O
• InChI: InChI=1S/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H
• InChIKey: ABMYEXAYWZJVOV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (pyridin-3-yl)boronic acid
• IUPAC Traditional name: pyridin-3-ylboronic acid
• Synonyms: pyridin-3-ylboranediol; Pyridine-3-boronic acid; 3-Pyridylboronic acid; Dihydroxy(3-pyridyl)borane; Pyridin-3-ylboronic acid; 3-Pyridineboronic acid; 3-Pyridinylboronic acid; 3-Pyridinylboronic acid; pyridin-3-ylboronic acid; Pyridine-3-boronic acid; 3-吡啶硼酸; 吡啶-3-硼酸

Database IDs

• CAS Number: 1692-25-7
• EC Number: 000-000-0
• MDL Number: MFCD00674177; MFCD08061353
• Beilstein Number: 471943
• PubChem SID: 160970646; 24873612
• PubChem CID: 2734378

CALCULATED PROPERTIES

• Acid pKa: 8.380423
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.31800184
• LogD (pH = 7.4): 0.2847616
• Log P: 0.3279
• Molar Refractivity: 28.4466 cm^3
• Polarizability: 12.640589 Å^3
• Polar Surface Area: 53.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C
• Partition Coefficient: -0.312
• Hydrophobicity(logP): 0.098

Safety Information

• Storage Warning: Irritant; IRRITANT, KEEP COLD
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0%; 95%; 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C5H6BNO2

DETAILS

Apollo Scientific Ltd - OR4119

Note: NMR spectrum must be run in D2O.

Sigma Aldrich - 512125

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5, 25 g in glass bottle
Application
Reagent used for
• Phosphine-free Suzuki-Miyaura cross-coupling reactions1
• Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation2
• N-arylation using copper acetylacetonate catalyst3
• Copper-mediated cyanation and regioselective cyanation of electron-rich benzenes4 Reagent use in Preparation of
• New linear poly(phenylpyridyl) chains by Suzuki coupling5
• Oligopyridyl foldamers as mimics of a-helix twist6
• Many highly significant therapeutic enzymatic and kinase inhibitors and receptor antagonists7,8,9