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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Chlorobenzenes

Research Brief on Methyl 2-bromo-4-chlorophenylacetate (CAS: 115871-49-3) in Chemical and Biomedical Applications

Methyl 2-bromo-4-chlorophenylacetate (CAS: 115871-49-3) is a halogenated phenylacetate derivative that has garnered significant attention in recent years due to its versatile applications in pharmaceutical synthesis and chemical biology. This compound serves as a key intermediate in the synthesis of various bioactive molecules, including nonsteroidal anti-inflammatory drugs (NSAIDs) and agrochemicals. Recent studies have explored its potential as a building block for novel drug candidates, particularly in the development of kinase inhibitors and antimicrobial agents.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of Methyl 2-bromo-4-chlorophenylacetate in the synthesis of potent Bruton's tyrosine kinase (BTK) inhibitors. The researchers utilized this compound as a crucial intermediate to introduce the 2-bromo-4-chlorophenyl moiety, which significantly enhanced the binding affinity of the resulting inhibitors to BTK. The study reported IC50 values in the low nanomolar range, suggesting promising therapeutic potential for autoimmune diseases and B-cell malignancies.

In the field of antimicrobial research, a recent investigation published in Bioorganic & Medicinal Chemistry Letters (2024) highlighted the compound's role in developing novel quinolone derivatives. The 2-bromo-4-chlorophenyl group, introduced via Methyl 2-bromo-4-chlorophenylacetate, was found to improve the compounds' penetration through bacterial cell membranes and enhance their activity against drug-resistant strains of Staphylococcus aureus. The study reported a 4-8 fold increase in potency compared to first-generation quinolones.

From a chemical perspective, advances in synthetic methodologies have improved the production efficiency of Methyl 2-bromo-4-chlorophenylacetate. A 2023 patent (WO2023184567) disclosed a novel catalytic system for its synthesis, achieving yields exceeding 85% with excellent purity. This development addresses previous challenges in large-scale production, making the compound more accessible for pharmaceutical applications.

The safety profile of Methyl 2-bromo-4-chlorophenylacetate has been extensively studied, with recent toxicological assessments confirming its relative safety as a synthetic intermediate when proper handling protocols are followed. However, researchers emphasize the need for careful consideration of its reactive bromo and chloro substituents in process chemistry to minimize potential genotoxic impurities in final drug substances.

Looking forward, the unique structural features of Methyl 2-bromo-4-chlorophenylacetate continue to inspire novel applications. Current research directions include its incorporation into PROTAC (proteolysis targeting chimera) molecules and its use in developing covalent inhibitors targeting cysteine residues. These emerging applications highlight the compound's enduring relevance in medicinal chemistry and drug discovery.

• 66191-93-3(Benzenepropanoic acid, 2-bromo-5-chloro-, methyl ester)
• 455957-76-3(Methyl 2-(2-bromo-5-chlorophenyl)acetate)
• 57486-69-8(Methyl 2-(2-bromophenyl)acetate)
• 512786-36-6((2-BROMO-3-METHYL-PHENYL)-ACETIC ACID METHYL ESTER)
• 849934-94-7(METHYL 4-BROMO-2-CHLOROPHENYLACETATE)
• 185153-57-5(BENZENEACETIC ACID, 2-BROMO-6-CHLORO-4-METHYL-, METHYL ESTER)
• 81682-38-4(2-(2-bromo-5-chlorophenyl)acetic acid)
• 960305-70-8(methyl 2-(3-bromo-5-chlorophenyl)acetate)
• 52864-56-9(2-(2-bromo-4-chlorophenyl)acetic acid)
• 66191-92-2(BENZENEPROPANOIC ACID, 2-BROMO-4-CHLORO-, METHYL ESTER)