(6-bromopyridin-3-yl)boronic acid

• ChemBase ID: 12389
• Molecular Formular: C5H5BBrNO2
• Molecular Mass: 201.8137
• Monoisotopic Mass: 200.95967081
• SMILES: c1(ccc(cn1)B(O)O)Br
• Canonical SMILES: Brc1ccc(cn1)B(O)O
• InChI: InChI=1S/C5H5BBrNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H
• InChIKey: BCYWDUVHAPHGIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6-bromopyridin-3-yl)boronic acid
• IUPAC Traditional name: (6-bromopyridin-3-yl)boronic acid; 6-bromopyridin-3-ylboronic acid
• Synonyms: 2-Bromopyridine-5-boronic acid 97%; 2-Bromopyridine-5-boronic acid; 2-Bromopyridyl-5-boronic acid; 2-Bromo-5-pyridylboronic acid; 6-Bromopyridine-3-boronic acid; 2-Bromo-5-pyridineboronic acid; (6-bromopyridin-3-yl)boranediol; 2-Bromopyridine-5-boronic acid; 6-Bromo-3-pyridinylboronic acid; 6-溴吡啶-3-硼酸; 2-溴吡啶-5-硼酸; 6-溴-3-吡啶基硼酸

Database IDs

• CAS Number: 223463-14-7
• EC Number: 000-000-0
• MDL Number: MFCD03411558
• Beilstein Number: 9119918
• PubChem SID: 24884805; 160975696
• PubChem CID: 2762706

CALCULATED PROPERTIES

• Acid pKa: 8.351354
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.51659
• LogD (pH = 7.4): 1.4713871
• Log P: 1.5172
• Molar Refractivity: 36.9116 cm^3
• Polarizability: 15.63643 Å^3
• Polar Surface Area: 53.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 161 - 166°C; 161-166 °C; 161-166(dec.)°C; ca 165°C dec.
• Hydrophobicity(logP): 1.045

Safety Information

• Storage Warning: IRRITANT; Irritant/Light Sensitive/Store under Argon/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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; 95%; 96%; 97%; 98%
• Linear Formula: Br(C5H3N)B(OH)2

DETAILS

Sigma Aldrich - 666556

General description
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Iterative cross-coupling reactions for synthesis of non-cytotoxic terpyridines1
• The Garlanding approach for synthesis of phenyl-pyridyl scaffolds2
• Cyanation for synthesis of aromatic nitriles3
• Suzuki-Miyaura cross-coupling with dihalopyridines and dihalobipyridines4
• Petasis boronic Mannich reaction5