What Is Methyl 3-Amino-5-Bromo-4-Methylbenzoate?

Methyl 3-amino-5-bromo-4-methylbenzoate (CAS not confirmed in source material; see review flag) is a substituted benzoate ester in which a benzene ring carries three distinct substituents: a primary amine group at the 3-position, a bromine atom at the 5-position, and a methyl group at the 4-position, with the carboxylic acid function protected as its methyl ester. This arrangement of orthogonal reactive handles on a single aromatic scaffold makes the compound particularly attractive as a synthetic building block. The free amine can participate in amide coupling, diazotization, reductive amination, or condensation reactions, while the aryl bromide is an excellent partner in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings. The methyl ester can be hydrolyzed to the corresponding carboxylic acid or converted to other acyl derivatives under standard conditions.

Physical Properties and Handling

Methyl 3-amino-5-bromo-4-methylbenzoate is typically obtained as a solid at room temperature. Its melting point and exact solubility data should be confirmed against the certificate of analysis supplied with each lot (see review flag). The compound is generally soluble in common organic solvents including dichloromethane, ethyl acetate, tetrahydrofuran, and dimethyl sulfoxide, with limited solubility in water due to its predominantly lipophilic character.

Standard laboratory precautions apply when handling this reagent: work in a well-ventilated fume hood, wear appropriate personal protective equipment (gloves, safety glasses, lab coat), and avoid inhalation of dust or aerosols. As with all aromatic amine-containing compounds, consult the Safety Data Sheet (SDS) prior to use and comply with local regulations for handling and disposal of halogenated organic materials.

Storage and Stability

For long-term stability, Methyl 3-amino-5-bromo-4-methylbenzoate should be stored in a tightly sealed container, away from light, moisture, and incompatible materials such as strong oxidizers and strong acids. Storage at 2–8 °C or at room temperature under inert atmosphere is commonly recommended for aromatic amine–halide compounds of this class; however, users should verify the specific storage conditions stated on the product label and certificate of analysis supplied by Aladdin Scientific (see review flag). Upon removal from cold storage, allow the container to equilibrate to room temperature before opening to prevent moisture condensation on the solid.

Typical Synthetic Applications

The three orthogonal functional groups present in Methyl 3-amino-5-bromo-4-methylbenzoate enable a broad range of synthetic transformations, making it a valued intermediate in medicinal chemistry, agrochemical research, and materials science:

• Palladium-catalyzed cross-coupling: The aryl C–Br bond undergoes Suzuki–Miyaura coupling with boronic acids, Buchwald–Hartwig amination with secondary amines, and Sonogashira coupling with terminal alkynes, enabling rapid elaboration of the aromatic core.
• Amine functionalization: The primary amine can be acylated to form amides, converted to isocyanates, used in reductive amination sequences, or subjected to diazotization followed by Sandmeyer-type reactions to introduce other functionality.
• Ester manipulation: Saponification of the methyl ester gives the free carboxylic acid for further amide bond formation or decarboxylation chemistry.
• Heterocycle synthesis: The combination of amine and ester in proximity facilitates cyclization reactions to form benzimidazolones, indazolones, anthranilates, and related N-heterocyclic scaffolds.

These attributes make M731315 a practical choice when constructing complex molecular architectures in drug discovery and fine-chemical synthesis programs.

Ordering and Quality Information

Methyl 3-amino-5-bromo-4-methylbenzoate is available from Aladdin Scientific under catalog number M731315. To place an order, visit the Aladdin Scientific website, search by product name or SKU, and add the desired pack size to your cart. Bulk quantities and custom packaging may be available upon request; contact Aladdin Scientific's sales team for pricing and availability. Each lot is accompanied by a certificate of analysis detailing purity (typically assessed by HPLC or NMR), appearance, and relevant physicochemical data. For questions about specifications, regulatory documentation (SDS, COA), or order status, contact Aladdin Scientific customer service.