Description

2-Bromo-5-hydroxypyridine (CAS No. 55717-40-3) is a high-purity brominated pyridine derivative with the molecular formula C₅H₄BrNO and IUPAC name 6-bromopyridin-3-ol. This heterocyclic compound is a versatile building block in pharmaceutical, agrochemical, and materials science research. Its unique structure, featuring both a bromo substituent and a hydroxyl group on the pyridine ring, enables diverse functionalization for cross-coupling reactions, ligand synthesis, and medicinal chemistry applications. Available in >98% purity (HPLC), this compound is rigorously tested for consistency and stability, ensuring reliable performance in synthetic workflows. Suitable for use in Suzuki-Miyaura couplings, SNAr reactions, and as a precursor for complex heterocycles. Packaged under inert gas in amber glass vials to ensure long-term stability.

Properties

• CAS Number: 55717-40-3
• Complexity: 78.8
• IUPAC Name: 6-bromopyridin-3-ol
• InChI: InChI=1S/C5H4BrNO/c6-5-2-1-4(8)3-7-5/h1-3,8H
• InChI Key: PTEFNEALEPSHLC-UHFFFAOYSA-N
• Exact Mass: 172.94763
• Molecular Formula: C5H4BrNO
• Molecular Weight: 174.00
• SMILES: C1=CC(=NC=C1O)Br
• Topological: 33.1
• Monoisotopic Mass: 172.94763
• Synonyms: 2-Bromo-5-hydroxypyridine, 55717-45-8, 676-372-9, 6-Bromopyridin-3-ol, 55717-40-3, 6-Bromo-3-pyridinol, 6-bromo-3-hydroxypyridine, MFCD04114184, 6-Bromopyridin-3-ol (radical ion(1+)), 3-PYRIDINOL, 6-BROMO-, 3-Pyridinol, 6-bromo-,radical ion(1+) (9CI), 3-hydroxy-6-bromopyridine, 5-Hydroxy-2-bromopyridine, 2-bromo-5-hydroxy pyridine, 2-bromo-5-hydroxy-pyridine, SCHEMBL148620, 6-BROMO-PYRIDIN-3-OL, SCHEMBL3709047, SCHEMBL4351964, CHEMBL3236917, SCHEMBL29001805, DTXSID80971087, BCP22991, CS-D0986, BBL101234, STL555030, AKOS005146397, AC-1375, FB16203, PB15771, PS-5226, AC-25807, SY003237, 2-Bromo-5-hydroxypyridine radical ion(1+), DB-031542, B3657, A15649, EN300-103371, F9994-0689, Z1201622821

Application

2-Bromo-5-hydroxypyridine serves as a key intermediate in the synthesis of active pharmaceutical ingredients (APIs), particularly in the development of kinase inhibitors and antiviral agents. Its bromo group participates efficiently in palladium-catalyzed cross-coupling reactions, while the hydroxyl group allows for further derivatization via etherification or esterification. Researchers utilize this compound in the preparation of functionalized pyridine ligands for transition metal catalysis. In material science, it contributes to the development of organic electronic materials and metal-organic frameworks (MOFs).

Safety and Hazards

GHS Hazard Statements

• H302 (27.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (90.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (90.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (81.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (27.3%)
• Skin Irrit. 2 (90.9%)
• Eye Irrit. 2 (90.9%)
• STOT SE 3 (81.8%)

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