Chemical Identity and Physical Properties

7-Bromoisoquinoline (CAS 56101-37-2) belongs to the isoquinoline family of nitrogen-containing heterocyclic compounds. Its molecular formula is C₉H₆BrN with a molecular weight of approximately 208.05 g/mol. The compound features the isoquinoline bicyclic aromatic ring system — a benzene ring fused to a pyridine ring — with a bromine substituent located at the 7-position on the benzene ring.

In its pure form, 7-Bromoisoquinoline typically appears as an off-white to pale yellow crystalline solid. The presence of the electron-withdrawing bromine atom at the 7-position imparts distinct electronic properties to the ring system compared to the parent isoquinoline, modulating reactivity at both carbon and nitrogen sites. The compound is sparingly soluble in water but dissolves readily in common organic solvents such as dichloromethane, tetrahydrofuran, dimethylformamide, and ethanol.

The C–Br bond at the 7-position is the primary site of synthetic elaboration, making this compound an electrophilic partner or directing handle in a broad range of chemical transformations. The aromatic nitrogen at position 2 of the isoquinoline ring further provides a coordination site or hydrogen-bond acceptor relevant in both catalysis and ligand design.

Key Research and Synthetic Applications

7-Bromoisoquinoline is one of the most strategically valuable halogenated isoquinoline building blocks available to synthetic and medicinal chemists. Its applications span several major reaction classes:

• Palladium-catalyzed cross-coupling reactions: The aryl C–Br bond undergoes efficient Suzuki–Miyaura, Negishi, Stille, Buchwald–Hartwig, and Sonogashira coupling reactions, enabling rapid diversification of the isoquinoline core with aryl, heteroaryl, alkyl, amino, and alkynyl groups.
• C–H activation chemistry: The bromine substituent can serve as a directing or activating element in transition-metal-catalyzed C–H functionalization protocols, opening access to polycyclic and complex architectures.
• Medicinal chemistry programs: The isoquinoline nucleus is a privileged scaffold found in numerous natural products and approved pharmaceuticals. 7-Bromoisoquinoline provides a handle to introduce structural diversity at the 7-position, facilitating structure–activity relationship (SAR) studies.
• Coordination chemistry and ligand design: The pyridyl-type nitrogen of isoquinoline allows 7-Bromoisoquinoline derivatives to act as ligands for transition metals, relevant in the synthesis of catalysts and photoactive materials.
• Synthesis of natural product analogues: Isoquinoline-containing natural products — including certain alkaloids with demonstrated biological activity — can be accessed via 7-Bromoisoquinoline as a key intermediate.

Researchers should select the cross-coupling conditions (catalyst, ligand, base, solvent) appropriate for each specific transformation and consult primary literature for optimized protocols.

Safe Handling, Storage, and Disposal

As with all brominated organic reagents, appropriate safety precautions must be observed when working with 7-Bromoisoquinoline. Always consult the current Safety Data Sheet (SDS) before use.

Personal Protective Equipment (PPE): Wear chemical-resistant gloves (nitrile recommended), a laboratory coat, and safety glasses or goggles. When handling significant quantities or in poorly ventilated areas, use a fume hood to minimize inhalation of dust or vapors.

Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified), dry, and well-ventilated area away from direct light and incompatible materials such as strong oxidizers and strong bases. Proper labeling and segregation from incompatible chemicals are essential.

Stability: The compound is generally stable under recommended storage conditions. Protect from prolonged exposure to moisture and light to prevent decomposition or discoloration.

Disposal: Dispose of 7-Bromoisoquinoline and its solutions as halogenated organic waste in accordance with local, institutional, and national regulations. Do not pour down the drain. Use appropriately labeled waste containers and coordinate with your institution's environmental health and safety (EHS) office.

First Aid: In case of skin or eye contact, flush immediately with copious amounts of water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air. Refer to the SDS for complete emergency procedures.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 7-Bromoisoquinoline (SKU: B152696) as a research-grade reagent. Purity is assessed by standard analytical techniques including gas chromatography (GC) or high-performance liquid chromatography (HPLC), and the product is characterized by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). A certificate of analysis (CoA) confirming lot-specific purity and analytical data is available upon request or via the Aladdin website.

Recommended verification on receipt: Upon receiving the product, visually inspect the container for integrity. If the compound appears unusually discolored or if the seal is compromised, contact Aladdin Scientific customer service before use. For critical applications, re-analysis by in-house GC or HPLC is advisable.

Packaging: Available in multiple pack sizes to suit both exploratory research and larger-scale synthetic programs. Consult the product page for current pack sizes, pricing, and availability.

Ordering: Order directly through the Aladdin Scientific website or contact your regional representative. Provide SKU B152696 when placing orders to ensure correct product selection.