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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 Briefing on 2,3-Dichloro-6-fluorobenzyl bromide (CAS: 886497-51-4) in Chemical Biology and Pharmaceutical Applications

2,3-Dichloro-6-fluorobenzyl bromide (CAS: 886497-51-4) is a halogenated benzyl bromide derivative that has garnered significant attention in recent chemical biology and pharmaceutical research due to its versatile reactivity as an alkylating agent. This compound serves as a critical building block in the synthesis of various biologically active molecules, particularly in the development of kinase inhibitors and other targeted therapeutics. Recent studies have highlighted its utility in medicinal chemistry, where its unique electronic properties conferred by the chloro-fluoro substitution pattern enable selective modifications of complex molecular scaffolds.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's application in synthesizing novel Bruton's tyrosine kinase (BTK) inhibitors, where the 2,3-Dichloro-6-fluorobenzyl moiety was incorporated to enhance target binding affinity and metabolic stability. The researchers utilized this intermediate to develop irreversible inhibitors through selective cysteine targeting, achieving improved pharmacokinetic profiles compared to previous generations of inhibitors. Molecular docking studies revealed that the specific halogen pattern of this benzyl bromide derivative contributed to optimal hydrophobic interactions within the BTK active site.

In parallel developments, 2,3-Dichloro-6-fluorobenzyl bromide has shown promise in radiopharmaceutical applications. A recent publication in ACS Medicinal Chemistry Letters (2024) described its use as a precursor for fluorine-18 labeled PET tracers. The presence of the fluorine atom at the 6-position allows for straightforward isotopic exchange, enabling the development of novel diagnostic agents for neurological disorders. This approach has been particularly valuable in creating tracers for imaging neuroinflammation, where the compound's ability to cross the blood-brain barrier has been demonstrated in preclinical models.

The synthetic utility of this compound extends to materials science applications as well. Research published in Advanced Materials (2023) reported its incorporation into organic electronic materials, where the electron-withdrawing effects of the halogen substituents were exploited to tune the electronic properties of conjugated polymers. These materials showed exceptional performance in organic thin-film transistors, with the 2,3-Dichloro-6-fluorobenzyl group serving as an effective side-chain modifier that improved both solubility and charge transport characteristics.

From a safety and handling perspective, recent toxicological studies have provided updated guidelines for working with 2,3-Dichloro-6-fluorobenzyl bromide. A 2024 publication in Chemical Research in Toxicology characterized its reactivity profile and recommended specific handling protocols to minimize exposure risks. The studies confirmed that while the compound exhibits moderate acute toxicity (LD50 = 320 mg/kg in rats), proper personal protective equipment and engineering controls can effectively mitigate occupational hazards during laboratory-scale synthesis and processing.

Looking forward, the unique properties of 2,3-Dichloro-6-fluorobenzyl bromide continue to inspire innovative applications across multiple disciplines. Current research directions include its potential use in PROTAC (proteolysis targeting chimera) development, where its reactivity profile may enable novel linker chemistries, and in covalent drug discovery platforms that leverage its selective alkylation capabilities. The compound's commercial availability from major chemical suppliers has further facilitated its adoption in diverse research programs, ensuring its continued prominence in chemical biology and pharmaceutical development.

• 71916-82-0(4-Chloro-2-fluorobenzyl bromide)
• 71916-91-1(2-(bromomethyl)-4-chloro-1-fluoro-Benzene)
• 68220-26-8(2-(bromomethyl)-1-chloro-3-fluorobenzene)
• 90292-67-4(2-Chloro-3,6-Difluorobenzyl bromide)
• 261762-87-2(2-Chloro-6-fluoro-3-methylbenzyl bromide)
• 45767-66-6(2-Chloro-4-fluorobenzyl bromide)
• 916420-69-4(3,6-Dichloro-2-fluorobenzyl bromide)
• 261762-88-3(6-Chloro-2-fluoro-3-methylbenzyl Bromide)
• 1373921-07-3(6-Chloro-2,3-difluorobenzyl bromide)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)