1. Product Overview
3-(1-Bromoethyl)quinoline (CAS 1824027-43-1) is a quinoline-derived secondary alkyl bromide bearing a bromine-substituted ethyl side chain at the 3-position of the quinoline ring. Also referred to as 1-(quinolin-3-yl)ethyl bromide, it acts as a reactive electrophilic building block in organic synthesis and medicinal chemistry. The compound typically appears as an off-white to light yellow crystalline solid or powder, widely used for introducing the 3-substituted quinoline motif via nucleophilic substitution or cross-coupling, and as a precursor to 3-(1-hydroxyethyl)quinoline (CAS 53531-33-2) through substitution with hydroxide or related oxygen nucleophiles.
2. Key Features and Advantages
• Secondary alkyl bromide functionality enables efficient nucleophilic displacement (e.g., with amines, thiols, cyanides) and elimination/reduction pathways to access diverse 3-substituted quinolines.
• 3-Substituted quinoline core is a privileged scaffold in drug discovery, supporting SAR studies for antiviral, antibacterial, anticancer, and CNS-targeted programs.
• High purity grade (≥98%) ensures clean conversion in sensitive multi-step pharmaceutical intermediate workflows with minimal halogen-related byproducts.
• Compatible with standard Grignard, organolithium, and transition-metal-catalyzed cross-coupling conditions (with appropriate care for alkyl bromide lability).
• Well-defined solid form with established analytical profile (NMR, HPLC, GC-MS) for QC release in R&D and custom synthesis projects.
3. Main Applications
• Pharmaceutical intermediate for quinoline-based APIs, especially in programs requiring a 3-alkyl or 3-aminoalkyl quinoline substructure.
• Building block for constructing 3-substituted quinolines, quinoline-containing spirocycles, and fused N-heterocycles via SN2, elimination, or metal-mediated coupling.
• Precursor to 3-(1-hydroxyethyl)quinoline and derived ketones/aldehydes through substitution, oxidation, or reduction sequences.
• Used in CRO/CDMO custom synthesis and academic research for method development in alkyl bromide functionalization, C–H activation at quinoline 3-position, and heterocyclic library generation.
• Intermediate in agrochemical and dye chemistry where 3-alkylated quinoline motifs are relevant.
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 an inert atmosphere (nitrogen or argon) to minimize hydrolysis of the alkyl bromide and prevent darkening. For long-term storage, keep at –20 °C in desiccated conditions. Avoid contact with strong bases, nucleophiles, or elevated temperatures which can promote elimination (to vinyl quinoline) or premature substitution. Handle in a well-ventilated area with standard PPE (lab coat, nitrile gloves, safety glasses). Reseal promptly after use. Under recommended conditions, shelf life is typically 12–24 months; periodic HPLC/GC check advised due to alkyl bromide lability.
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 of vapor. Alkyl bromides can be irritating and may be absorbed through skin; handle as a reactive halogenated organic intermediate with standard precautions. Prevent dust/vapor generation. In case of skin contact, wash thoroughly with soap and water; for eye contact, rinse cautiously with plenty of water and seek medical advice if irritation persists. Avoid contact with strong bases or metals that may generate organometallic species. Dispose according to local regulations for halogenated organic laboratory chemicals. Always consult the latest SDS from the supplier before use.
