1. Product Overview
3-Bromo-5-methoxyquinoline (CAS 1416438-38-4) is a di-substituted quinoline derivative bearing a bromine atom at the 3-position and a methoxy group at the 5-position of the quinoline nucleus. Also referred to as Quinoline, 3-bromo-5-methoxy-, it serves as a versatile electrophilic building block in medicinal chemistry and heterocyclic synthesis. The compound typically appears as an off-white to light yellow crystalline solid or pale yellow solid at room temperature, widely used for constructing quinoline-based active pharmaceutical ingredients (APIs), kinase inhibitors, antimalarial agents, and anti-infectives via regioselective cross-couplings at C3–Br and optional demethylation or nucleophilic aromatic substitution at C5–OMe. Its quinoline core is a privileged scaffold in drug discovery with broad bioactivity across CNS, antiviral, and anticancer programs.
2. Key Features and Advantages
• Regioselective reactivity: 3-bromo is highly active in Suzuki, Sonogashira, and Buchwald–Hartwig cross-couplings for late-stage diversification; 5-methoxy stabilizes the ring and can be demethylated to 5-hydroxy under strong Lewis acid or BBr₃ conditions for O-functionalization.
• Quinoline scaffold is a classic pharmacophore in drug discovery (antimalarials like chloroquine analogs, kinase inhibitors, antibacterials), enabling rapid SAR exploration via C3 arylation/alkynylation and C5-O manipulation.
• High purity grade (≥97%) ensures clean conversion in multi-step pharmaceutical workflows with minimal halogen-related impurities.
• Stable solid form at RT (sealed in dry, room temperature storage acceptable per supplier data), facilitating accurate weighing, handling, and QC by HPLC, NMR, and LC-MS.
• Compatible with standard protecting-group strategies (quinoline N-oxidation/reduction) and orthogonal halogen vs. ether reactivity in library synthesis.
3. Main Applications
• Pharmaceutical intermediate for quinoline-based drug candidates, especially antimalarial, kinase inhibitor, antiviral, and antibacterial R&D where 3,5-disubstituted quinolines are key pharmacophores.
• Building block for 3-arylated/alkynylated-5-methoxyquinolines via Pd-catalyzed cross-couplings at C3–Br, followed by optional demethylation to 5-hydroxyquinolines for ether/ester formation.
• Intermediate in CRO/CDMO custom synthesis and academic research for quinoline library generation, C–H activation studies, and heterocyclic method development (Miyaura borylation to boronic esters, then Suzuki).
• Precursor to 5-methoxyquinolin-3-ylboronic acids/esters and further to diversified 3,5-disubstituted quinolines relevant to agrochemical and material science programs.
• Used in fragment-based drug design to introduce a 3-bromo-5-methoxyquinoline handle for Pd-catalyzed linkage to aromatic/aliphatic fragments via cross-coupling.
4. Technical Specifications
5. Storage and Handling
Store in a cool, dry place at 2–8 °C in a tightly sealed, light-protected container under desiccated conditions; sealed in dry at room temperature is also acceptable per common supplier recommendations for long-term stability. For extended storage, keep at –20 °C under an inert atmosphere to minimize moisture uptake and slow halogen hydrolysis. The aryl bromide is stable under neutral conditions but should be protected from strong nucleophiles, bases, or prolonged exposure to humid air which may promote hydrolysis of C–Br. Handle in a well-ventilated area with standard PPE (lab coat, nitrile gloves, safety glasses). Reseal promptly after use. Under recommended dry conditions, shelf life is typically 24 months.
6. Safety Overview
Intended for research and synthetic use only; not for direct human or veterinary therapeutic administration. May cause irritation to eyes, skin, and respiratory tract upon contact or dust inhalation (GHS07: H302/H315/H319/H335). Halogenated methoxy-quinolines can be mildly irritating to mucous membranes; handle as a fine organic powder/solid with standard laboratory precautions. Prevent dust generation. In case of skin contact, wash thoroughly with soap and water; for eye contact, rinse cautiously with plenty of water for several minutes and seek medical advice if irritation persists. Avoid contact with strong bases or nucleophiles unless intentionally performing a reaction. Dispose according to local regulations for halogenated heterocyclic organic laboratory chemicals. Always consult the latest SDS from the supplier before use.
