(pyridin-4-yl)boronic acid

• ChemBase ID: 7438
• Molecular Formular: C5H6BNO2
• Molecular Mass: 122.91764
• Monoisotopic Mass: 123.04915884
• SMILES: c1cc(ccn1)B(O)O
• Canonical SMILES: OB(c1ccncc1)O
• InChI: InChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H
• InChIKey: QLULGIRFKAWHOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (pyridin-4-yl)boronic acid
• IUPAC Traditional name: pyridin-4-ylboronic acid
• Synonyms: Pyridin-3-yl-boronic Acid; (3-Pyridinyl)boronic Acid; 3-Pyridylboronic Acid; Dihydroxy(3-pyridyl)borane; 3-Pyridineboronic Acid; B-4-Pyridinylboronic Acid; 4-Pyridinylboronic Acid; 4-Pyridineboronic Acid; B-3-Pyridinylboronic Acid; pyridin-4-ylboronic acid; 4-Pyridylboronic acid; 4-Pyridineboronic acid; 4-Pyridinylboronic acid; 4-Boronopyridine; Pyridine-4-boronic acid; Pyridine-4-boronic acid hydrate; 4-吡啶硼酸; 吡啶-4-硼酸; 吡啶-4-硼酸水合物

Database IDs

• CAS Number: 1692-25-7; 1692-15-5
• EC Number: 000-000-0
• MDL Number: MFCD01074545; MFCD08061353
• Beilstein Number: 471944
• PubChem SID: 24882629; 160970745
• PubChem CID: 2734379

CALCULATED PROPERTIES

• Acid pKa: 8.55551
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.3270008
• LogD (pH = 7.4): 0.2987032
• Log P: 0.3279
• Molar Refractivity: 28.4466 cm^3
• Polarizability: 12.641157 Å^3
• Polar Surface Area: 53.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Light Yellow Powder
• Melting Point: >300 °C(lit.); >300°C; >300°C

Safety Information

• Storage Warning: IRRITANT, KEEP COLD; Irritant/Air Sensitive/Moisture Sensitive/Store under Argon/Store at -20°C
• 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
• Storage Temperature: -20°C

Product Information

• Purity: 90%; 95%; 95+%; 97%; 98%; ca 10-15% water
• Empirical Formula (Hill Notation): C5H6BNO2

DETAILS

Sigma Aldrich - 634492

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5, 25 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura coupling reactions1
• Ligand-free palladium-catalyzed Suzuki coupling reaction under microwave irradation2 Reagent used in Preparation of
• HIV-1 protease inhibitors3
• Potential cancer threapeutics, such as PDK1 and protein kinase CK2 inhibitors4,5

Toronto Research Chemicals - P991355

Boronic acid derivatives and their binding affinities with diols.

Toronto Research Chemicals - P991350

Boronic acid derivatives and their binding affinities with diols.

REFERENCES

• Yang, W., et al.: Bioorg. Med. Chem. Lett., 12, 2175 (2002)
• Yang, W., et al.: Med. Res. Rev., 23, 346 (2002)
• Yang, W., et al.: Bioorg. Med. Chem. Lett., 12, 2175 (2002)
• Yang, W., et al.: Med. Res. Rev., 23, 346 (2002)