8-Bromo-6-chloroquinoline: Properties, Uses & FAQs

8-Bromo-6-chloroquinoline is a dihalogenated quinoline building block widely employed in palladium-catalyzed cross-coupling reactions and heterocyclic synthesis programs.

CAS Number

Needs verification — not confirmed in source material

Molecular Formula

C9H5BrClN

Molecular Weight

Approximately 242.50 g/mol (needs verification)

SKU / Catalog Number

B181936

Key Functional Groups

C-8 bromo, C-6 chloro substituents on a quinoline scaffold

Primary Application

Selective cross-coupling and nucleophilic aromatic substitution in medicinal and materials chemistry

What Is 8-Bromo-6-chloroquinoline and Why Is It Useful?

8-Bromo-6-chloroquinoline is a bicyclic heteroaromatic compound consisting of a benzene ring fused to a pyridine ring, bearing a bromine atom at position 8 and a chlorine atom at position 6. The presence of two distinct halogen substituents at different ring positions makes this compound a versatile synthon: the C–Br bond at the sterically distinct peri-position (C-8) and the C–Cl bond at C-6 can be addressed selectively under appropriately tuned reaction conditions.

This selectivity is particularly valuable in medicinal chemistry and materials science, where sequential functionalization of the two halogen handles allows the stepwise introduction of diverse fragments onto the quinoline core, enabling rapid generation of compound libraries or construction of complex architectures.

Reactivity and Synthetic Applications

The two halogen substituents in 8-Bromo-6-chloroquinoline display inherently different reactivity. The C–Br bond is generally more reactive than the C–Cl bond toward oxidative addition into palladium(0) or nickel(0) catalysts, enabling chemoselective Suzuki–Miyaura, Negishi, Kumada, Buchwald–Hartwig, and Sonogashira cross-coupling reactions at C-8 while preserving the C–Cl bond for subsequent transformations.

The C–Cl bond at C-6 can subsequently undergo palladium-catalyzed coupling under more forcing conditions or participate in nucleophilic aromatic substitution (SNAr) reactions with nitrogen, oxygen, or sulfur nucleophiles, owing to the electron-withdrawing effect of the quinoline nitrogen that activates the ring toward SNAr. This orthogonal reactivity makes 8-Bromo-6-chloroquinoline particularly attractive for the synthesis of unsymmetrically substituted quinoline derivatives used as kinase inhibitors, fluorescent materials, and ligands for metal coordination chemistry.

Storage, Handling, and Safety Considerations

As a halogenated aromatic compound, 8-Bromo-6-chloroquinoline should be handled with appropriate personal protective equipment including nitrile gloves, safety glasses, and a lab coat. Work should be performed in a well-ventilated fume hood to avoid inhalation of dust or vapors.

For storage, the compound should be kept in a tightly sealed container away from moisture, heat, and strong oxidizing or reducing agents. Storage at room temperature in a cool, dry place is generally recommended for solid haloquinolines; however, researchers should consult the specific Safety Data Sheet (SDS) and Certificate of Analysis (CoA) provided with lot B181936 for confirmed storage temperature and shelf-life data. Specific hazard classifications, GHS pictograms, and first-aid measures are detailed in the product SDS available from Aladdin Scientific.

Purity, Specification, and Quality Assurance

Aladdin Scientific supplies 8-Bromo-6-chloroquinoline under catalog number B181936. The exact purity specification, available pack sizes, and analytical data (including HPLC purity, NMR confirmation of structure, and GC data where applicable) are documented in the Certificate of Analysis issued for each manufacturing lot.

Researchers requiring high-purity material for sensitive biological assays or catalyst studies should request the lot-specific CoA prior to use. If a particular purity grade or custom quantity is required, Aladdin's technical and sales teams can be contacted to discuss options. All specifications stated on the product page should be verified against the accompanying CoA before critical experimental use.

Ordering and Technical Support

8-Bromo-6-chloroquinoline (B181936) can be ordered directly through the Aladdin Scientific website. Customers can search by catalog number, CAS number, or compound name. Volume pricing, bulk quantities, and custom synthesis inquiries are handled by the Aladdin sales team.

For technical questions regarding suitable reaction conditions, compatible coupling partners, or analytical methods for characterizing derivatives, Aladdin's scientific support staff are available to assist. SDS documents, CoAs, and additional product documentation can be downloaded from the product detail page or requested via customer service.

Frequently asked questions

What makes 8-Bromo-6-chloroquinoline useful as a synthetic building block?

The compound carries two chemically distinct halogen leaving groups—bromine at C-8 and chlorine at C-6—that can be addressed selectively in sequence. The C–Br bond typically reacts preferentially in palladium-catalyzed cross-coupling reactions, while the C–Cl bond can be utilized in subsequent coupling or SNAr steps, enabling efficient, divergent construction of substituted quinoline libraries.

How should I store 8-Bromo-6-chloroquinoline to maintain its stability?

The compound should be stored in a tightly sealed container in a cool, dry location away from moisture and strong oxidizing agents. Consult the lot-specific Certificate of Analysis and Safety Data Sheet supplied with catalog number B181936 for confirmed storage temperature recommendations and shelf-life information.

Can the C–Cl bond be selectively coupled while preserving the C–Br bond?

Selective activation of C–Cl over C–Br in the same molecule is challenging because the C–Br bond is inherently more reactive toward most transition-metal catalysts. Achieving C–Cl selectivity may require specialized catalysts, bulky ligands, or SNAr conditions. Researchers are advised to consult the primary literature on chemoselective cross-coupling of polyhalogenated heteroarenes for specific protocols.

What is the catalog number for 8-Bromo-6-chloroquinoline at Aladdin Scientific?

8-Bromo-6-chloroquinoline is listed under catalog number B181936 at Aladdin Scientific. You can search for this SKU directly on the Aladdin website to access the product page, pricing, stock availability, and downloadable documentation.

Is 8-Bromo-6-chloroquinoline suitable for use in Suzuki–Miyaura coupling reactions?

Yes, the C–Br bond of 8-Bromo-6-chloroquinoline is well-suited for Suzuki–Miyaura coupling with aryl or heteroaryl boronic acids under standard palladium catalysis conditions, allowing selective introduction of a boronic acid-derived fragment at C-8 while the C–Cl bond is retained for further functionalization. Specific catalyst systems, bases, and solvents should be optimized based on the coupling partner employed.

References

1. General reference on chemoselective cross-coupling of polyhalogenated heteroarenes — specific literature citation not available in source material; needs expert review.
2. Aladdin Scientific product page for 8-Bromo-6-chloroquinoline, catalog number B181936. Aladdin Scientific (accessed 2024).

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.