Description

2-Bromopyridine-5-boronic acid (CAS No. 223463-14-7) is a high-purity boronic acid derivative with the molecular formula C₅H₅BBrNO₂, widely utilized in organic synthesis and pharmaceutical research. This compound, also known by its IUPAC name (6-bromopyridin-3-yl)boronic acid, features a bromine substituent at the 2-position of the pyridine ring, enhancing its reactivity in cross-coupling reactions such as Suzuki-Miyaura couplings. Its boronic acid functional group makes it an essential building block for constructing complex heterocyclic frameworks. Suitable for researchers and industrial applications, this reagent is rigorously tested for quality, ensuring optimal performance in catalytic processes. Available in various quantities, it is stored under recommended conditions to maintain stability and purity.

Properties

• CAS Number: 223463-14-7
• Complexity: 114
• IUPAC Name: (6-bromo-3-pyridyl)boronic acid
• InChI: InChI=1S/C5H5BBrNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H
• InChI Key: BCYWDUVHAPHGIP-UHFFFAOYSA-N
• Exact Mass: 200.95967
• Molecular Formula: C5H5BBrNO2
• Molecular Weight: 201.82
• SMILES: B(C1=CN=C(C=C1)Br)(O)O
• Topological: 53.4
• Monoisotopic Mass: 200.95967
• Synonyms: 223463-14-7, 2-Bromopyridine-5-boronic acid, DTXSID70376380, DTXCID20327408, 672-028-7, (6-bromopyridin-3-yl)boronic Acid, 6-BROMOPYRIDINE-3-BORONIC ACID, 2-Bromo-5-pyridineboronic Acid, BPBA, 2-Bromopyridyl-5-boronic acid, MFCD03411558, 6-BROMO-3-PYRIDINYLBORONIC ACID, 6-Bromopyridin-3-ylboronic acid, 2-bromo-5-pyridine boronoc acid, 2-Bromo-5-pyridylboronic acid, Boronic acid, (6-bromo-3-pyridinyl)-, 6-Bromo-3-pyridylboronic Acid, 6-Bromo-pyridine-3-boronic acid, (6-bromo-3-pyridinyl)boronic acid, 6-BROMOPYRIDIN-3-YL-3-BORONIC ACID, SCHEMBL181140, CHEMBL3236616, (6-bromopyridin-3-yl)boronicAcid, BCP28751, SBB052564, AKOS002670073, AB14131, AC-6991, CS-W015531, GS-6517, HY-W014815, PD158316, SY017261, 6-Bromo-3-pyridinylboronic acid, >=95%, DB-024860, B3307, EN300-107963, Z1269166001, 6-Bromopyridine-3-boronic acid(contains varying amounts of Anhydride)

Application

2-Bromopyridine-5-boronic acid is primarily employed in palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura couplings, to form biaryl or heteroaryl structures. It serves as a key intermediate in the synthesis of pharmaceutical compounds, agrochemicals, and advanced materials. Researchers also utilize it in the development of ligands for catalysis and functionalized polymers. Its reactivity makes it valuable for modifying pyridine-based scaffolds in medicinal chemistry.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (90%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (90%)

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