1. Product Overview
3-Bromo-5-fluoroquinoline (CAS 1416439-00-3) is a dihalogenated quinoline derivative bearing a bromine atom at the 3-position and a fluorine atom at the 5-position of the quinoline nucleus. Also referred to as Quinoline, 3-bromo-5-fluoro-, it serves as a versatile electrophilic and cross-coupling building block in medicinal chemistry and heterocyclic synthesis. The compound typically appears as a white to off-white crystalline powder or solid at room temperature, widely used for constructing quinoline-based active pharmaceutical ingredients (APIs), kinase inhibitors, and anti-infective agents via regioselective functionalization: the C3-bromide is highly reactive in Suzuki, Sonogashira, and Buchwald–Hartwig cross-couplings, while the C5-fluorine offers a handle for nucleophilic aromatic substitution or remains as a metabolically stabilizing fluoro substituent in drug scaffolds.
2. Key Features and Advantages
• Regioselective reactivity: 3-bromo is preferentially engaged in Pd-catalyzed cross-couplings; 5-fluoro is less labile but available for SNAr with strong nucleophiles or retained as a bioisostere in final API.
• Quinoline core is a privileged heterocycle in drug discovery (antimalarials, kinase inhibitors, antibacterials, CNS agents), enabling rapid SAR exploration via C3 diversification.
• High purity grade (≥98%) ensures clean conversion in multi-step pharmaceutical workflows with minimal halogen-related byproducts.
• Stable crystalline solid form facilitates accurate weighing, handling, and QC by HPLC, NMR (characteristic aromatic signals), and GC-MS.
• Compatible with standard protecting-group strategies (quinoline N-oxidation/reduction) and orthogonal halogen reactivity in library synthesis.
3. Main Applications
• Pharmaceutical intermediate for quinoline-based drug candidates, especially kinase inhibitors, antimalarial, antiviral, and antibacterial R&D where 3,5-disubstituted quinolines are key pharmacophores.
• Building block for 3-arylated/alkynylated-5-fluoroquinolines via Suzuki, Sonogashira, and Stille couplings at C3, followed by optional SNAr at C5-F.
• Intermediate in CRO/CDMO custom synthesis and academic research for quinoline library generation, C–H activation studies, and heterocyclic method development.
• Precursor to 5-fluoroquinoline-3-boronic esters (via Miyaura borylation) 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-fluoroquinoline 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, room temperature also acceptable per supplier data; refrigeration preferred for long-term). 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 the C–Br bond. Handle in a well-ventilated area with standard PPE (lab coat, nitrile gloves, safety glasses). Reseal promptly after use. Under recommended dry, refrigerated 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 (typical GHS07 profile: H315/H319/H335). Halogenated quinolines can be mildly irritating to mucous membranes; handle as a fine organic powder 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.
