Chemical Identity and Structural Features

3-Bromo-5-methylpyridin-4-amine (molecular formula C₆H₇BrN₂, approximate molecular weight 187.04 g/mol) is a substituted aminopyridine featuring three key functional elements on a six-membered aromatic ring: a bromine atom at position 3, a methyl group at position 5, and a primary amine (–NH₂) at position 4, with a ring nitrogen at position 1. This combination of substituents makes the compound an electronically differentiated heterocyclic scaffold.

The aryl bromide moiety is the primary handle for metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings, enabling efficient C–C and C–N bond formation. The ring nitrogen and the exocyclic amino group provide two distinct sites for further functionalization, hydrogen-bond donation/acceptance, and coordination chemistry. The methyl group at position 5 introduces steric bias and moderate electron-donating character, influencing regioselectivity in subsequent transformations.

These structural features make 3-Bromo-5-methylpyridin-4-amine a highly versatile fragment for the construction of complex heterocyclic architectures found in bioactive molecules and functional materials.

Storage, Handling and Safety Guidelines

Storage: Store 3-Bromo-5-methylpyridin-4-amine in a tightly sealed container in a cool, dry, well-ventilated area, away from direct light and moisture. Unless the product-specific datasheet specifies otherwise, storage at 2–8 °C or room temperature under inert atmosphere (nitrogen or argon) is generally recommended for halogenated amines to minimise oxidation of the amine and hydrolysis of the C–Br bond over extended periods. Always consult the current Aladdin product datasheet (SKU B590874) for lot-specific storage conditions.

Handling: Work with this compound in a chemical fume hood. Wear appropriate personal protective equipment including nitrile or neoprene gloves, safety goggles, and a laboratory coat. Aromatic amines as a compound class warrant careful handling; avoid inhalation of dust or vapours and skin contact. Wash hands thoroughly after handling.

Disposal: Dispose of residues in accordance with local regulations governing halogenated organic waste. Do not discharge into drains or the environment. Consult the Safety Data Sheet (SDS) for full hazard classification and first-aid measures before use.

Note: Specific GHS hazard classification and SDS data for this compound should be verified against the current Aladdin SDS document. Refer to review flags below.

Research Applications in Medicinal and Synthetic Chemistry

Cross-Coupling Chemistry: The aryl bromide of 3-Bromo-5-methylpyridin-4-amine is well-suited for palladium- and nickel-catalyzed cross-coupling reactions. Suzuki–Miyaura coupling with boronic acids or esters installs aryl, heteroaryl, or vinyl substituents at C-3, providing rapid access to biaryl and heteroaryl frameworks that are prevalent in drug candidates and agrochemicals. Buchwald–Hartwig amination allows C–N bond formation at the C-3 position, expanding the accessible chemical space.

Pharmaceutical Intermediate: Aminopyridine and bromopyridine motifs appear frequently in kinase inhibitors, antiviral agents, and CNS-active compounds. The 4-amino group can serve as a handle for amide bond formation, urea/carbamate synthesis, or cyclisation to form fused ring systems such as pyrrolopyridines, imidazopyridines, and pyridopyrimidines — scaffolds commonly explored in drug discovery programmes.

Fragment-Based Drug Discovery (FBDD): As a low-molecular-weight, functionally rich fragment, 3-Bromo-5-methylpyridin-4-amine is suitable for fragment library construction and hit-expansion strategies, where the bromine and amine act as orthogonal handles for iterative elaboration.

Material Science: Pyridine-amine hybrids have utility as ligands in coordination polymers and metal–organic frameworks (MOFs), and as components in functional organic materials.

Quality, Purity and Procurement Guidance

Specification: Aladdin Scientific supplies 3-Bromo-5-methylpyridin-4-amine under SKU B590874 (internal reference BD:BD35537). Researchers should request the current Certificate of Analysis (CoA) to verify purity (typically assessed by HPLC or GC), identity (confirmed by NMR and/or MS), and appearance before use in sensitive synthetic steps.

Purity Considerations: For medicinal chemistry and high-throughput screening applications, a purity of ≥95% (HPLC) is generally recommended. Lower purity grades may be acceptable for exploratory synthesis where downstream purification is planned.

Quantities and Packaging: Contact Aladdin Scientific sales or consult the product page for available pack sizes, pricing, and lead times. Bulk quantities may be available upon request.

Ordering: Place orders directly through the Aladdin Scientific website or contact the regional sales team. Reference SKU B590874 to ensure correct product selection. For regulatory compliance (e.g., export control, customs documentation), consult the procurement and shipping teams.