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4-Bromo-2-fluoro-N-methylbenzamide is a specialized organic intermediate widely utilized in the pharmaceutical and agrochemical industries for the synthesis of complex bioactive molecules. With the Chemical Abstracts Service (CAS) registry number 1368507-68-9, this compound features a benzamide core substituted with a bromine atom at the para position and a fluorine atom at the ortho position relative to the carbonyl group, alongside an N-methyl substituent. Its molecular formula is C8H7BrFNO, yielding a precise molecular weight of approximately 246.05 g/mol. The presence of both halogen atoms significantly enhances its reactivity profile, making it an ideal scaffold for transition-metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig amination. These transformations are pivotal in constructing biaryl structures found in modern therapeutics.
In drug discovery, this molecule serves as a critical building block for developing kinase inhibitors, antidepressants, and anti-inflammatory agents. The electron-withdrawing nature of the fluorine and bromine substituents modulates the electronic properties of the aromatic ring, often improving metabolic stability and binding affinity when incorporated into final drug candidates. Furthermore, the N-methyl group can influence conformational flexibility and lipophilicity, optimizing pharmacokinetic profiles. Researchers frequently employ this reagent to access diverse heterocyclic systems through cyclization protocols. Due to its specific substitution pattern, it offers a unique pathway for introducing structural diversity early in the lead optimization phase. While primarily used in laboratory-scale research, high-purity grades are essential for ensuring reproducible results in medicinal chemistry campaigns. Safety data indicates standard handling precautions for halogenated aromatics, including avoidance of skin contact and inhalation. As the demand for novel small-molecule therapies grows, intermediates like 4-Bromo-2-fluoro-N-methylbenzamide remain indispensable tools for chemists aiming to accelerate the development of next-generation medicines.