Description

5-Bromo-2-hydroxypyridine-3-carbonitrile (CAS No. 405224-22-8) is a high-purity heterocyclic organic compound with the molecular formula C₆H₃BrN₂O. This specialized chemical is a valuable intermediate in pharmaceutical and agrochemical research, particularly in the synthesis of bioactive molecules. The compound features a bromo-substituted pyridine core with hydroxyl and cyano functional groups, offering versatile reactivity for cross-coupling reactions, nucleophilic substitutions, and heterocyclic scaffold modifications. Available in >95% purity (HPLC), it is supplied as a crystalline solid with strict quality control to ensure batch-to-batch consistency. Proper storage at 2-8°C under inert conditions is recommended to maintain stability. Suitable for use in medicinal chemistry, material science, and as a ligand precursor in catalysis.

Properties

• CAS Number: 405224-22-8
• Complexity: 281
• IUPAC Name: 5-bromo-2-oxo-1H-pyridine-3-carbonitrile
• InChI: InChI=1S/C6H3BrN2O/c7-5-1-4(2-8)6(10)9-3-5/h1,3H,(H,9,10)
• InChI Key: SWTLLSLCDHXNIU-UHFFFAOYSA-N
• Exact Mass: 197.94288
• Molecular Formula: C6H3BrN2O
• Molecular Weight: 199.00
• SMILES: C1=C(C(=O)NC=C1Br)C#N
• Topological: 52.9
• Monoisotopic Mass: 197.94288
• Synonyms: 5-bromo-2-hydroxypyridine-3-carbonitrile, 800-559-8, 405224-22-8, 5-Bromo-2-hydroxynicotinonitrile, 5-BROMO-3-CYANO-2(1H)-PYRIDINONE, 5-bromo-2-oxo-1H-pyridine-3-carbonitrile, 5-bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile, 5-Bromo-3-Cyano-2-Hydroxypyridine, MFCD07363806, 3-Pyridinecarbonitrile, 5-bromo-1,2-dihydro-2-oxo-, SCHEMBL459834, SCHEMBL3069301, DTXSID10428392, SWTLLSLCDHXNIU-UHFFFAOYSA-N, 5-bromo-3-cyano-2(1h)-pyridone, MFCD13184828, SBB092404, AKOS005072724, AKOS013153971, AC-9427, FS-3771, GC-0703, PB30875, SY021373, DB-070032, EN300-127450, W11573, 5-Bromo-2-oxo-1,2 dihydro-pyridine-3-carbonitrile, 5-Bromo-2-oxo-1,2-dihydro-pyridine-3-carbonitrile, 5-Bromo-3-cyano-2-hydroxypyridine, 5-Bromo-2-hydroxypyridine-3-carbonitrile

Application

This compound serves as a key building block in the synthesis of pharmaceutical candidates, particularly kinase inhibitors and antiviral agents. Researchers utilize its reactive bromo and cyano groups for palladium-catalyzed cross-couplings in drug discovery programs. The hydroxyl functionality allows for further derivatization to create diverse pyridone-based scaffolds. In material science, it finds application as a precursor for functionalized heterocyclic polymers with optoelectronic properties.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): 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, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• Acute Tox. 4 (100%)
• STOT SE 3 (100%)

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