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4-Bromo-2-hydroxypyridine
1. Basic Information
Name: 4-Bromo-2-hydroxypyridine
Alias: 4-Bromopyridin-2-ol
CAS No.: 36953-37-4
Molecular Formula: C5H4BrNO
Molecular Weight: 173.99
Category: Brominated pyridine heterocyclic pharmaceutical intermediate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Off-white to pale beige crystalline powder
- Odor: Faint heterocyclic odor
- Solubility: Soluble in methanol, ethanol, DMSO, THF, ethyl acetate; slightly soluble in hot water; insoluble in alkanes
- Melting Range: 210–215 °C
- Hygroscopy: Slightly hygroscopic under high humidity
- Aqueous Property: Weakly acidic aqueous solution due to pyridinol hydroxyl group
Chemical Properties
- Molecular Structure: Pyridine ring with bromine at 4-position and hydroxyl group at 2-position, exists in pyridone tautomer form
- Hydroxyl Reactivity: Capable of O-alkylation, esterification, and condensation reactions
- Aryl Bromide Activity: C-Br bond participates in Suzuki, Buchwald, Sonogashira cross-coupling reactions
- Thermal Stability: Stable below 120 °C; slight decomposition upon long heating above melting point
- Photostability: Sensitive to ultraviolet light; long-term light exposure causes darkening
- Compatibility: Compatible with polar organic solvents; incompatible with strong oxidants and concentrated strong alkali
3. Main Application Fields
1. Pharmaceutical Synthetic Intermediate (Core Application)
Key building block for constructing pyridine-containing anti-inflammatory, anti-tumor and kinase inhibitor APIs via palladium-catalyzed coupling reactions
2. Agrochemical Intermediate
Raw material for halogenated pyridine fungicides and insecticides
3. HPLC Reference Standard
Reference substance for detection of bromopyridinol intermediates
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 36953-37-4 |
| Molecular Formula | C5H4BrNO |
| Appearance | Off-white crystalline powder |
| HPLC Purity | Synthetic Intermediate Grade ≥99.0% |
| Water Content (KF) | ≤0.30% |
| Melting Range | 210–215 °C |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber vacuum aluminum foil bags / PE-lined fiber drums |
| Storage Condition | Hermetically sealed dark warehouse below 25 °C; isolated from light, oxidants and alkaline reagents |
| Transportation Requirement | Light-sensitive bromopyridine solid, fully sealed light-proof packaging |
| Shelf Life | 24 months under nitrogen-filled vacuum packaging |
Safety Warning
Irritant brominated pyridine powder. Dust irritates eyes, respiratory tract and skin; prolonged skin contact may trigger allergic dermatitis. All operations must be conducted in ventilated fume hoods with dust respirators, chemical-resistant gloves and full-face safety goggles. Store airtight away from light to avoid photooxidation discoloration. Waste liquid needs solvent recovery and neutralization; solid waste belongs to organic hazardous waste and shall be disposed by licensed professional institutions.
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