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• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Research Briefing on 2-(4-bromo-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 1326316-85-1) in Chemical Biology and Pharmaceutical Applications

2-(4-bromo-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 1326316-85-1) is a boronic ester derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a critical intermediate in Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology for constructing carbon-carbon bonds in drug discovery and materials science. The presence of both bromo and fluoro substituents on the phenyl ring enhances its reactivity and selectivity, making it a valuable building block for the synthesis of complex bioactive molecules.

Recent studies have highlighted the role of this boronic ester in the development of novel kinase inhibitors, particularly targeting tyrosine kinases involved in cancer progression. A 2023 publication in the Journal of Medicinal Chemistry demonstrated its utility in the synthesis of BTK (Bruton's tyrosine kinase) inhibitors, showing improved pharmacokinetic properties compared to earlier generations of compounds. The electron-withdrawing fluorine atom at the ortho position was found to significantly influence the compound's metabolic stability, addressing previous challenges with rapid clearance.

In the field of PET (positron emission tomography) tracer development, researchers have utilized 1326316-85-1 as a precursor for fluorine-18 labeled compounds. The bromine substituent allows for efficient radiohalogenation via isotopic exchange, while the boronic ester moiety enables subsequent cross-coupling reactions to create diverse molecular scaffolds. A recent Nature Communications paper (2024) described its application in creating novel σ2 receptor ligands for imaging tumor hypoxia, demonstrating superior in vivo stability and target specificity.

The compound's unique structural features have also been exploited in materials science applications. A 2024 Advanced Materials report detailed its use as a monomer in the synthesis of conjugated polymers for organic electronics. The fluorine substitution pattern was found to modulate the polymer's band gap, while the boronic ester functionality facilitated precise control over polymer chain length and end-group composition.

From a synthetic chemistry perspective, recent advances have focused on improving the preparation and handling of this sensitive boronic ester. A 2023 Organic Process Research & Development article presented an optimized large-scale synthesis protocol that minimizes protodeboronation side reactions, achieving >95% purity with excellent reproducibility. This development is particularly significant for industrial applications where batch-to-batch consistency is crucial.

In conclusion, 2-(4-bromo-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane continues to demonstrate remarkable versatility across multiple research domains. Its unique combination of reactive handles (bromo, fluoro, and boronic ester) makes it an indispensable tool for medicinal chemists and materials scientists alike. Future research directions may explore its potential in targeted drug delivery systems and as a scaffold for covalent inhibitor development, particularly in addressing emerging drug resistance mechanisms.

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• 863868-37-5(2,6-Difluorophenylboronic acid, pinacol ester)
• 408492-24-0(2,2',2''-(2,4,6-Trifluorobenzene-1,3,5-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane))
• 325143-04-2(4,4,5,5-TETRAMETHYL-2-(2,4,6-TRIFLUOROPHENYL)-1,3,2-DIOXABOROLANE)
• 876062-39-4(2-(2-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 303006-90-8(2-[2,5-difluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1400220-51-0(2-(3-Bromo-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 942069-49-0(5-Bromo-2-fluoro-1,3-phenylenediboronic acid, pinacol ester)
• 1073339-12-4(5-Bromo-2,3-difluorophenylboronic Acid Pinacol Ester)
• 288101-48-4(2,4-Difluorophenylboronic acid, pinacol ester)