What Is 5-Bromo-2-(chloromethyl)pyridine Hydrochloride?

5-Bromo-2-(chloromethyl)pyridine hydrochloride (Aladdin SKU B733676) is a heteroaromatic halide supplied as its stable hydrochloride salt. The free base contains a pyridine ring bearing a bromine substituent at the 5-position and a chloromethyl (–CH₂Cl) group at the 2-position.

The hydrochloride salt form improves bench stability relative to the free base, reducing spontaneous decomposition and making the compound easier to weigh and handle in air for short periods. Researchers should nonetheless handle the material promptly and return it to sealed storage after use.

Because the molecule carries two distinct electrophilic sites—the aryl C–Br bond amenable to palladium-catalysed cross-coupling and the highly reactive benzyl chloride—it serves as a versatile bifunctional linker or intermediate in multi-step organic synthesis.

How Should This Reagent Be Stored and Handled Safely?

Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated location. Protect from moisture, as the hygroscopic hydrochloride salt can absorb water, potentially affecting purity and reactivity. Refrigerated storage (2–8 °C) is commonly recommended for long-term preservation; confirm the specific recommendation on the Certificate of Analysis (CoA) supplied with your lot.

Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves, laboratory coat, and eye protection when handling this compound. The benzyl chloride moiety is a potent alkylating agent and potential lachrymator; all operations should be conducted in a well-ventilated fume hood.

Incompatibilities: Keep away from strong bases, nucleophiles, and oxidising agents, which can trigger uncontrolled alkylation or decomposition. Consult the Safety Data Sheet (SDS) available from Aladdin Scientific for full hazard information before use.

What Are the Key Synthetic Applications?

N- and O-Alkylation: The electrophilic benzyl chloride group reacts readily with amines, alcohols, thiols, and other nucleophiles under mild base conditions, making B733676 a convenient reagent for attaching the 5-bromopyridin-2-ylmethyl pharmacophore to target scaffolds.

Palladium-Catalysed Cross-Coupling: The aryl bromide at C-5 undergoes standard Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and related cross-coupling reactions, enabling introduction of aryl, heteroaryl, alkyl, or amino groups while the chloromethyl handle is preserved or orthogonally protected.

Pharmaceutical and Agrochemical Intermediates: Pyridine-based building blocks bearing halogens at defined positions are broadly used in the synthesis of kinase inhibitors, CNS-active compounds, and crop-protection agents. The dual-halogen functionality of this compound allows sequential derivatisation in convergent synthesis strategies.

Heterocycle Construction: Intramolecular cyclisation reactions exploiting both the benzyl chloride and the ring nitrogen or an introduced nucleophile can afford fused bicyclic heterocycles of medicinal interest.

Solubility, Purity, and Analytical Considerations

Solubility: As a hydrochloride salt, this compound shows improved water solubility compared to the free base. It is also soluble in polar organic solvents such as DMSO, DMF, and methanol. Solubility in non-polar solvents is limited. Always confirm solubility under your specific reaction conditions before scale-up.

Purity Verification: Each lot of B733676 is accompanied by a Certificate of Analysis (CoA) stating purity by HPLC or other appropriate method. Researchers requiring additional characterisation may employ ¹H NMR, ¹³C NMR, or mass spectrometry. Note that the HCl salt proton appears in the low-field region of the ¹H NMR spectrum and should be accounted for in stoichiometric calculations.

Moisture Sensitivity: Opened containers should be re-sealed promptly and stored with desiccant to prevent hydrolysis of the benzyl chloride to the corresponding alcohol, which would reduce reagent potency and introduce impurities.

Ordering, Availability, and Technical Support

How to Order: 5-Bromo-2-(chloromethyl)pyridine hydrochloride is available from Aladdin Scientific under catalog number B733676. Place orders through the Aladdin Scientific website, your regional distributor, or by contacting the Aladdin sales team directly. Bulk or custom quantities may be available upon request.

Documentation: Safety Data Sheets (SDS) and Certificates of Analysis (CoA) for specific lot numbers are available for download on the product page or by request from customer service. Always review the SDS before first use.

Technical Inquiries: For questions about analytical data, synthetic protocols, or custom synthesis services involving this building block, contact Aladdin Scientific technical support. Our team can assist with solubility screening, formulation advice, and referrals to application literature.