1. Product Overview
3-Vinylquinoline (CAS 67752-31-2) is a quinoline-derived vinyl arene featuring an ethenyl group at the 3-position of the quinoline nucleus. Also referred to as 3-ethenylquinoline, it serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, where the electron-rich quinoline system combined with the terminal alkene enables diverse cycloaddition, polymerization, and electrophilic/nucleophilic functionalization strategies. The compound typically appears as a pale yellow to light brown liquid at room temperature or a low-melting solid upon cooling, widely used for introducing the 3-substituted quinoline motif into active pharmaceutical ingredients (APIs), kinase inhibitor scaffolds, and conjugated materials in research settings.
2. Key Features and Advantages
• Terminal vinyl group supports Diels–Alder cycloadditions, Heck couplings, hydroboration, epoxidation, and radical polymerizations for scaffold elaboration.
• 3-Substituted quinoline core is a privileged heterocycle in drug discovery (antiviral, anticancer, antimicrobial, CNS programs), enabling rapid SAR exploration.
• High purity grade (≥98%) ensures clean conversion in sensitive multi-step pharmaceutical workflows with minimal quinoline-related impurities.
• Compatible with standard protecting-group strategies (N-oxidation/reduction of quinoline nitrogen) and orthogonal functionalization of the vinyl vs. aromatic system.
• Well-characterized by NMR, HPLC, and GC-MS; liquid form facilitates accurate syringe-based dosing in small-scale synthesis and high-throughput screening.
3. Main Applications
• Pharmaceutical intermediate for quinoline-based drug candidates, especially in kinase inhibitor, antiviral, and anticancer R&D where 3-vinyl or 3-ethyl/3-ethylidene quinolines are target motifs.
• Building block for Diels–Alder cyclizations to access fused quinoline–cyclohexene or quinoline–aromatic hybrids in medicinal chemistry and materials science.
• Monomer or co-monomer in radical polymerizations for quinoline-containing conjugated polymers and fluorescent probe development.
• Intermediate in CRO/CDMO custom synthesis and academic research for method development in Heck/Suzuki couplings of vinyl arenes, C–H activation at quinoline 3-position, and heterocyclic library generation.
• Precursor to 3-ethylquinoline, 3-(2-hydroxyethyl)quinoline, and 3-acetylquinoline derivatives through hydrogenation, hydroboration/oxidation, or ozonolysis/Wacker oxidation sequences.
4. Technical Specifications
5. Storage and Handling
Store in a cool, dry place at 2–8 °C in a tightly sealed, light-protected amber vial under an inert atmosphere (nitrogen or argon) to prevent oxidation of the vinyl group and photoinduced dimerization or polymerization. For long-term storage, keep at –20 °C in desiccated conditions; the compound is air- and light-sensitive as a liquid vinyl arene. Avoid exposure to strong acids, Lewis acids, or radical initiators which may catalyze polymerization. Handle in a well-ventilated area with standard PPE (lab coat, nitrile gloves, safety glasses). Use promptly after opening; periodic GC check advised due to gradual oxidation. Under recommended conditions, shelf life is typically 12–18 months when protected from air and light.
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 vapor/dust inhalation. Vinyl arenes and quinolines can be irritating and potentially sensitizing; handle as a reactive, air-sensitive aromatic alkene with standard laboratory precautions. Prevent vapor generation and avoid breathing vapors. 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. Keep away from heat, sparks, open flames, and strong oxidizers. Dispose according to local regulations for non-halogenated aromatic organic laboratory chemicals. Always consult the latest SDS from the supplier before use.
