Chemical Identity and Physical Properties

6-Bromoquinoline-3-carbonitrile (CAS registry number should be confirmed; SKU B190538) is an aromatic heterocyclic compound belonging to the quinoline family. Its molecular formula is C₁₀H₅BrN₂ with a molecular weight of approximately 233.06 g/mol. The structure consists of a fused benzene–pyridine bicyclic system with a bromine substituent at the 6-position and a nitrile (–CN) group at the 3-position.

The presence of two electron-withdrawing groups—the ring nitrogen and the 3-cyano group—renders the aromatic system significantly electron-deficient. This electronic character enhances the reactivity of the C-6 aryl bromide toward oxidative addition in transition-metal-catalyzed cross-coupling reactions. The compound is expected to be a solid at room temperature with a relatively high melting point consistent with similar bromoquinoline derivatives; precise melting point data should be confirmed from the certificate of analysis supplied with each lot.

The nitrile group at C-3 can participate in further synthetic transformations, including hydrolysis to carboxylic acid or amide, reduction to primary amine, cycloaddition to tetrazole, or condensation reactions to form heterocyclic rings, substantially expanding the synthetic utility of this scaffold.

Synthesis and Reactivity

6-Bromoquinoline-3-carbonitrile serves as a dual-handle building block in synthetic chemistry. The aryl bromide at C-6 is well-suited for palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura, Negishi, Sonogashira, Buchwald–Hartwig amination, and Heck reactions. These transformations allow rapid diversification of the quinoline core to introduce aryl, alkenyl, alkynyl, amino, and other functional groups at C-6.

Simultaneously, the 3-cyano group provides orthogonal reactivity. Under appropriate conditions it can be converted to: (1) a primary amine via catalytic hydrogenation or reduction with reducing agents such as DIBAL-H; (2) a carboxylic acid or ester via acidic or basic hydrolysis; (3) an amidine via reaction with hydroxylamine followed by dehydration; or (4) a tetrazole ring via [3+2] cycloaddition with sodium azide, a transformation valued in medicinal chemistry for bioisosteric replacement of carboxylic acids.

The electron-deficient quinoline nitrogen also enables nucleophilic aromatic substitution (S_NAr) at activated positions under forcing conditions, and the compound may serve as a ligand precursor or coordinate to Lewis acids in catalytic applications. Researchers are advised to optimize reaction conditions empirically, as the dual electrophilic handles require careful selectivity control.

Applications in Medicinal and Materials Chemistry

Medicinal Chemistry: Quinoline is a privileged scaffold in drug discovery, appearing in antimalarial agents, antibacterials, kinase inhibitors, and antiviral compounds. The 3-carbonitrile substitution pattern is particularly valuable because the nitrile group can interact with biological targets through dipole interactions and hydrogen bonding with backbone amide NH groups or active-site residues. 6-Bromoquinoline-3-carbonitrile can be employed as a starting material to synthesize focused libraries of quinoline-based bioactive candidates by coupling diverse boronic acids, amines, or other nucleophiles at C-6 while retaining or further elaborating the C-3 nitrile.

Kinase Inhibitor Design: Cyanoquinoline derivatives have been reported as scaffolds in the design of receptor tyrosine kinase (RTK) inhibitors. The 3-cyano group can mimic the hydrogen-bond acceptor role and contribute to selectivity. Researchers exploring EGFR, VEGFR, or related kinase targets may find this compound a useful precursor.

Materials Science: Electron-deficient quinoline derivatives are of interest in organic electronics as components of n-type semiconductors, fluorescent probes, and metal-chelating ligands for luminescent materials. The combination of bromine (enabling further coupling) and the nitrile group (tuning LUMO energy) makes 6-Bromoquinoline-3-carbonitrile a candidate monomer or building block for conjugated polymers and small-molecule emitters.

Safe Handling, Storage, and Disposal

Hazard Overview: As with most organobromine and nitrile-containing aromatic compounds, 6-Bromoquinoline-3-carbonitrile should be treated as a potential irritant and harmful substance. Specific GHS classification and hazard statements should be confirmed from the Safety Data Sheet (SDS) provided by Aladdin Scientific for lot B190538. In the absence of specific toxicological data, apply the precautionary principle.

Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile gloves), safety goggles, and a laboratory coat when handling. If fine powder generation is likely, use a respiratory mask rated for fine particulates (P2/N95 or equivalent) and conduct manipulations in a fume hood.

Storage: Store in a tightly sealed container in a cool (recommended 2–8 °C or room temperature per SDS), dry, and well-ventilated location away from incompatible materials such as strong oxidizers, strong bases, and reducing agents. Protect from prolonged exposure to light and moisture, which may cause decomposition or hydrolysis of the nitrile group.

Disposal: Dispose of waste material and contaminated items in accordance with local, regional, and national regulations for chemical waste. Do not pour down the drain. Contact your institution's environmental health and safety office for guidance on approved disposal routes for halogenated organic compounds.

Quality, Purity, and Ordering Information

Specification: Aladdin Scientific supplies 6-Bromoquinoline-3-carbonitrile under SKU B190538. Researchers should consult the current product page or contact technical support for the most up-to-date purity specification, available pack sizes, and pricing. Purity is typically assessed by HPLC and/or NMR; the certificate of analysis (CoA) accompanying each lot provides lot-specific analytical data including purity, appearance, and identity confirmation.

Quality Assurance: Each batch is subject to internal quality control procedures. The CoA should be requested and reviewed before use in critical assays. If the compound does not meet stated specifications, contact Aladdin Scientific customer service to initiate a return or replacement under the applicable returns and refunds policy.

Ordering: Place orders through the Aladdin Scientific website, authorized distributors, or by contacting the sales team directly. For bulk quantities or custom synthesis inquiries, reach out to technical sales. Ensure that your institution's procurement and import regulations for organobromine compounds are met prior to ordering, particularly for international shipments.