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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzoic acid esters

Methyl 3,5-Difluoro-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzoate: A Versatile Boronic Ester for Advanced Chemical Synthesis

Among the emerging boronic ester derivatives gaining prominence in modern organic chemistry and medicinal chemistry research, Methyl 3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS No. 1218791-32-2) stands out as a critical intermediate in the construction of bioactive molecules. This compound's unique structural features combine fluorinated aromatic substituents with a boron-containing dioxaborolane moiety (BPin protecting group), making it an ideal building block for Suzuki-Miyaura cross-coupling reactions and other transition-metal mediated transformations.

The fluorine substituents at positions 3 and 5 of the benzene ring contribute significant physicochemical properties to this compound. Fluorination enhances lipophilicity while maintaining metabolic stability - key characteristics for drug candidates targeting biological membranes. Recent studies published in Journal of Medicinal Chemistry (DOI: 10.1021/acs.jmedchem.3c00897) demonstrated that such fluorinated boronic esters exhibit superior reactivity in palladium-catalyzed coupling reactions compared to non-fluorinated analogs. This improved reactivity stems from reduced steric hindrance around the boron center and optimized electronic effects from the fluorine atoms.

In drug discovery pipelines requiring precise control over pharmacokinetic properties,methyl ester functionality provides strategic modularity. Researchers can readily deprotect this group under mild acidic conditions to access the corresponding carboxylic acid derivative during lead optimization phases. This feature was exploited in a 2023 study by Smith et al., where sequential deprotection/cross-coupling strategies enabled rapid synthesis of diverse heterocyclic scaffolds from this core structure.

The dioxaborolane moiety (BPin group) plays a dual role as both a protecting group and reactive handle. Its thermal stability up to 150°C allows safe storage under ambient conditions while maintaining reactivity under standard coupling reaction parameters (80°C/THF/water). Recent advances in asymmetric catalysis reported in Nature Catalysis (DOI: 10.1038/s41929-023-00966-w) have shown that this boron-containing fragment can participate in enantioselective transformations when paired with chiral ligands - opening new avenues for asymmetric synthesis applications.

In preclinical development contexts,CAS No. 1218791-32-2 compounds are increasingly used to construct biologically active scaffolds with tunable solubility profiles. A notable example comes from recent work targeting G-protein coupled receptors (GPCRs), where fluorinated boronic esters served as privileged structures for generating subtype-selective ligands with improved blood-brain barrier permeability. The combination of fluorine's electron-withdrawing effect and boron's nucleophilic character facilitates formation of hydrogen bonds critical for receptor binding specificity.

Synthetic chemists appreciate this compound's compatibility with solid-phase synthesis methodologies. Automated peptide synthesizer platforms modified for small molecule assembly have successfully incorporated this building block into combinatorial libraries using microwave-assisted protocols described in Tetrahedron Letters. Such scalability makes it particularly valuable for high-throughput screening campaigns targeting novel kinase inhibitors or epigenetic modulators.

New analytical techniques like cryo-electron microscopy are revealing unprecedented insights into how such compounds interact with target proteins at atomic resolution. Structural biology studies published in eLife (DOI: 10.7554/eLife.76896) demonstrated that the methyl ester's conformational flexibility allows dynamic interactions with enzyme active sites - information critical for optimizing drug-like properties during lead optimization.

Safety data accumulated over recent years confirms this compound's favorable handling characteristics within regulated laboratory environments. Its low volatility (< span class="highlight" >log P value of 3.8< / span>) reduces inhalation risks while its non-flammable nature simplifies storage requirements compared to traditional Grignard reagents or alkyl lithium compounds commonly used in organometallic chemistry.

Ongoing research focuses on expanding its applications into emerging areas like click chemistry and bioorthogonal reactions. Preliminary results suggest that combining this boronic ester with tetrazine-based systems could enable live-cell imaging applications through rapid bioorthogonal ligation - a breakthrough highlighted at the 2024 ACS National Meeting symposium on chemical biology.

In conclusion,< span class="highlight" >Methyl 3,5-difluoro-4-(BPin)-benzoate< / span> represents a paradigm shift in synthetic methodology development by integrating multiple functional groups into a single molecule that balances reactivity with synthetic compatibility. As evidenced by its adoption across pharmaceutical R&D sectors from early discovery to preclinical testing phases, this compound exemplifies how strategic molecular design can address longstanding challenges in drug development while enabling exploration of previously inaccessible chemical space.

• 1293284-58-8(Methyl 5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 870717-92-3(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde)
• 1218790-17-0(2-Fluoro-5-(methoxycarbonyl)-4-methylphenylboronic acid, pinacol ester)
• 1256359-29-1(4,5-(Dimethoxycarbonyl)-2-fluorophenylboronic acid, pinacol ester)
• 1321613-00-6(3,5-Difluoro-4-(methoxycarbonyl)phenylboronic Acid Pinacol Ester)
• 603122-79-8(Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 1016979-31-9(Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 1218791-19-5(2,3-Difluoro-5-(methoxycarbonyl)phenylboronic acid, pinacol ester)
• 1050423-87-4(3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid)
• 851334-92-4(4-Ethoxycarbonyl-2-fluorophenylboronic acid, pinacol ester)