6-bromo-8-fluoro-2-methylquinoline | CAS 958650-94-7

PRODUCT OVERVIEW

 

6-bromo-8-fluoro-2-methylquinoline | CAS 958650-94-7 is a highly specialized heterocyclic intermediate used predominantly in medicinal chemistry, agrochemical research, and advanced material synthesis. Characterized by a quinoline core substituted with bromine, fluorine, and methyl functionalities, this compound serves as a versatile building block for the development of novel small molecules with potential pharmacological activity.

Quinolines are a class of nitrogen-containing aromatic compounds with well-established utility in drug discovery. The strategic placement of halogen substituents — bromine at position 6 and fluorine at position 8 — along with a methyl group at position 2, imparts unique electronic, steric, and physicochemical properties that can profoundly influence biological activity, metabolic stability, and binding affinity when incorporated into target compounds.

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CHEMICAL SPECIFICATIONS

 

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KEY FEATURES & ADVANTAGES

 

High Purity and Consistency

Manufactured under strict quality controls, 6-Bromo-8-Fluoro-2-Methylquinoline is supplied with a high degree of purity (≥98%), ensuring reliability and reproducibility in research and development workflows.

Strategic Functionalization

• Bromine (Br) at the 6-position enables efficient cross-coupling reactions (e.g., Suzuki, Heck, Buchwald-Hartwig), a cornerstone for constructing complex heterocycles and biaryl systems.

• Fluorine (F) at the 8-position modulates electronic density and improves metabolic resilience in drug candidates.

• Methyl (CH₃) at the 2-position provides desirable steric and lipophilic effects, influencing binding interactions.

Versatile Intermediate

This compound is an ideal substrate for derivatization, facilitating rapid exploration of structure-activity relationships (SAR) across chemical libraries.

Research and Development Focus

Valuable for synthetic chemists engaged in:

• Lead optimization

• Medicinal chemistry programs

• Heterocyclic scaffolding

• Fluorine-containing compound design

• Agrochemical innovation

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SYNTHETIC UTILITY

 

6-Bromo-8-Fluoro-2-Methylquinoline’s unique substitution pattern makes it a prime candidate for a range of synthetic transformations:

Cross-Coupling Reactions

The bromine substituent readily participates in palladium-catalyzed coupling reactions with organoboron, organostannane, and organozinc reagents. These reactions build complexity with high regioselectivity.

Nucleophilic Aromatic Substitution (S_NAr)

The presence of fluorine on the quinoline ring enhances opportunities for nucleophilic aromatic substitution, particularly with heteroatom nucleophiles, enabling the installation of amines, alkoxides, or thiol groups.

C–H Functionalization Approaches

Emerging catalytic methodologies allow for direct C–H activation around the quinoline core, expanding the synthetic toolbox for diversifying quinoline derivatives.

Heterocycle Expansion & Ring-Closing Strategies

This intermediate can be transformed into fused bicyclic or polycyclic frameworks, which are essential motifs in many bioactive compounds.

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APPLICATIONS of 6-bromo-8-fluoro-2-methylquinoline | CAS 958650-94-7 :

 

Medicinal Chemistry

Quinoline derivatives have a long history of biological relevance, featuring in antimalarials, antivirals, anticancer agents, and CNS-active compounds. The incorporation of bromine and fluorine substituents can:

• Improve binding affinity

• Increase lipophilicity

• Enhance metabolic stability

• Modulate pKa and solubility

These qualities make 6-Bromo-8-Fluoro-2-Methylquinoline valuable for lead discovery and optimization campaigns.

Agrochemical Research

Halogenated quinoline scaffolds have been investigated for herbicidal, insecticidal, and fungicidal properties. This intermediate offers a pathway toward novel agrochemicals with improved efficacy and environmental profiles.

Material Science

Functionalized quinolines serve as precursors in the synthesis of organic electronic materials, dyes, ligands for coordination chemistry, and fluorophores for imaging applications.

SAR Library Development

This compound enables the construction of focused libraries for exploratory screening, particularly where halogen bonding and aromatic interactions are of interest.

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ANALYTICAL CHARACTERIZATION

 

Each batch of 6-Bromo-8-Fluoro-2-Methylquinoline is characterized using a suite of analytical techniques to ensure identity and purity:

• High-Performance Liquid Chromatography (HPLC) — purity assessment

• Nuclear Magnetic Resonance (NMR) spectroscopy — structural confirmation

• Mass Spectrometry (MS) — molecular weight verification

• Elemental Analysis — composition validation

Certificates of Analysis (CoAs) are available with each order, documenting batch-specific results.

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SAFETY & HANDLING

 

6-Bromo-8-Fluoro-2-Methylquinoline should be handled by trained personnel in a well-equipped laboratory environment:

• Use appropriate personal protective equipment (gloves, goggles, lab coat).

• Avoid inhalation, ingestion, and contact with skin or eyes.

• Store in a cool, dry area, tightly sealed away from incompatible agents.

• Consult the Safety Data Sheet (SDS) before use for hazard classifications, first-aid measures, and disposal guidelines.

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CUSTOM SERVICES

 

ResolveMass Laboratories Inc. offers tailored services to support your projects, including:

• Custom synthesis

• Scale-up processing

• Analytical method development

• Purity optimization

Contact our technical support team for project consultation and bulk pricing.