(5-bromopyridin-3-yl)boronic acid

• ChemBase ID: 12390
• Molecular Formular: C5H5BBrNO2
• Molecular Mass: 201.8137
• Monoisotopic Mass: 200.95967081
• SMILES: c1c(cc(cn1)B(O)O)Br
• Canonical SMILES: OB(c1cncc(c1)Br)O
• InChI: InChI=1S/C5H5BBrNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H
• InChIKey: ICCGFOKNFZWCTJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5-bromopyridin-3-yl)boronic acid
• IUPAC Traditional name: 5-bromopyridin-3-ylboronic acid
• Synonyms: 3-Bromo-5-pyridylboronic acid; 3-Bromopyridyl-5-boronic acid; 5-bromopyridine-3-boronic acid; (3-Bromopyridin-5-yl)boronic acid; (5-Bromo-3-pyridyl)boronic acid; (5-bromo-3-pyridinyl)boronic acid; 5-Bromopyridine-3-boronic acid; 5-Bromopyridine-3-boronic acid 96%; 3-BROMOPYRIDINE-5-BORONIC ACID; 5-溴吡啶-3-硼酸

Database IDs

• CAS Number: 452972-09-7
• EC Number: 000-000-0
• MDL Number: MFCD02685634
• Beilstein Number: 9119873
• PubChem SID: 160975697
• PubChem CID: 3814811

CALCULATED PROPERTIES

• Acid pKa: 8.29968
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1188105
• LogD (pH = 7.4): 1.0684228
• Log P: 1.1197
• Molar Refractivity: 36.0694 cm^3
• Polarizability: 15.589177 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; 260 (dec.); 273-275°C

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: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; 97%; 98%; tech. 85%
• Empirical Formula (Hill Notation): C5H5BBrNO2

DETAILS

Sigma Aldrich - 686816

General description
May contain varying amounts of anhydride.
Packaging
1, 5 g in glass bottle
Application
Reactant for preparation of:
• Thienylpyridyl garlands via cross-coupling with heteroaryl halides1
• Arenes via nickel-catalyzed cross-coupling with potassium aryl- and heteroaryl trifluoroborates2
• Meso-substituted ABCD-type porphyrins by functionalization reactions3
• Analogs of (acetylamino)(dimethylpyrazol)(pyridyl)pyrimidines as A2A adenosine receptor antagonists for the treatment of Parkinson′s disease4
• 5-hydroxy-1,3,2-dioxaborolan-4-ones boronate-amine complexes via heterocyclization with α-oxocarboxylic acids followed by subsequent complexation5
• Radioligands with optimized brain kinetics for PET imaging of nAChR6