What Is 3-Bromo-5-chloro-2-methyl-aniline?

3-Bromo-5-chloro-2-methyl-aniline is a substituted aromatic amine bearing two halogen substituents (bromine at position 3 and chlorine at position 5) and a methyl group ortho to the primary amine at position 2. This substitution pattern creates a sterically and electronically differentiated scaffold that is highly valuable in synthetic chemistry.

The compound belongs to the class of halogenated anilines, which are established building blocks in pharmaceutical and agrochemical synthesis. The presence of both an aryl bromide and an aryl chloride on the same ring provides two orthogonal handles for selective cross-coupling chemistry, such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi reactions, enabling step-wise elaboration of the aromatic core.

Handling, Storage, and Safety

As with all aromatic amines, 3-bromo-5-chloro-2-methyl-aniline should be handled with appropriate personal protective equipment, including nitrile gloves, safety glasses, and a laboratory coat. Operations involving weighing or dissolution of the compound should be conducted in a well-ventilated fume hood.

The compound should be stored in a tightly sealed container, away from light, heat, and moisture, typically at room temperature or under refrigeration (2–8 °C) as indicated by the supplier's certificate of analysis. Prolonged exposure to air may lead to oxidative discoloration. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use for full hazard classification and first-aid measures.

Applications in Synthetic and Medicinal Chemistry

3-Bromo-5-chloro-2-methyl-aniline serves as a key intermediate in the synthesis of pharmaceutically active compounds and agrochemicals. Its primary amine group can participate in amide bond formation, reductive amination, diazotization, and condensation reactions, while the aryl halides enable transition-metal-catalyzed cross-coupling reactions.

The orthogonal reactivity of the C–Br and C–Cl bonds (bromine being more reactive toward oxidative addition in most palladium-catalyzed systems) allows chemists to selectively functionalize one position before the other, enabling the construction of complex biaryl and heterocyclic frameworks commonly found in drug candidates. This compound is therefore frequently used in fragment-based drug discovery and lead optimization campaigns.

Purity, Quality, and Analytical Characterization

Aladdin Scientific supplies 3-bromo-5-chloro-2-methyl-aniline (SKU: B682583) as a research-grade reagent. Lot-specific purity data and analytical certificates are available upon request or via the product page. Typical characterization techniques for this compound include:

• 1H and 13C NMR spectroscopy — confirms substitution pattern and absence of regioisomeric impurities.
• GC or HPLC purity analysis — quantifies overall chemical purity.
• Mass spectrometry (MS) — verifies molecular weight and isotope pattern consistent with a mono-bromo, mono-chloro species.

Researchers are advised to confirm purity by independent analysis when the compound is used in sensitive biological assays or structure–activity relationship (SAR) studies.

Ordering and Technical Support

3-Bromo-5-chloro-2-methyl-aniline is available from Aladdin Scientific under SKU B682583. Orders can be placed through the Aladdin Scientific website, by contacting your regional sales representative, or through authorized distributors.

For technical questions regarding compatibility, recommended reaction conditions, or custom quantities, please contact the Aladdin Scientific technical support team. Bulk pricing and custom packaging options may be available for institutional or industrial customers. Always request a current SDS and certificate of analysis (CoA) at the time of ordering.