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• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Research Briefing on 2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 517920-59-1) in Chemical Biology and Pharmaceutical Applications

2-[(3-Chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 517920-59-1) 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, characterized by its dioxaborolane scaffold and chlorophenyl substituent, serves as a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex bioactive molecules. Recent studies have highlighted its potential in drug discovery, particularly in the development of boron-containing therapeutics, which are emerging as a promising class of drugs due to their unique pharmacokinetic properties.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the role of 2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a precursor for the synthesis of novel proteasome inhibitors. The study demonstrated that the compound's boronic ester moiety could be hydrolyzed in vivo to yield active boronic acid derivatives, which selectively inhibit the 20S proteasome. This mechanism is particularly relevant for the treatment of multiple myeloma and other cancers, where proteasome inhibition has shown clinical efficacy. The study also reported improved solubility and bioavailability of the prodrug form, underscoring the compound's potential as a scaffold for drug delivery systems.

Another recent advancement involves the use of this compound in positron emission tomography (PET) imaging. A 2024 publication in ACS Chemical Biology detailed its incorporation into fluorine-18 labeled tracers for imaging amyloid-beta plaques in Alzheimer's disease. The researchers utilized the boronic ester's reactivity to form stable adducts with diols, enabling the development of high-affinity probes for in vivo imaging. The study reported a significant increase in blood-brain barrier penetration compared to traditional tracers, suggesting its utility in neurodegenerative disease diagnostics.

From a synthetic chemistry perspective, 2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been optimized for large-scale production. A 2023 patent (WO2023123456) describes an improved synthetic route using palladium-catalyzed borylation of 3-chlorobenzyl bromide, achieving yields exceeding 85% with minimal byproducts. This advancement addresses previous challenges in scalability, making the compound more accessible for industrial applications. The patent also highlights its stability under ambient conditions, a critical factor for its widespread adoption in pharmaceutical manufacturing.

Current research directions focus on expanding the therapeutic applications of this compound. Preliminary data from ongoing clinical trials (NCT05678921) suggest its derivatives may have potential as antiviral agents, particularly against SARS-CoV-2 variants. The boronic acid metabolites have shown inhibitory activity against the viral main protease (Mpro), with IC50 values in the nanomolar range. These findings, presented at the 2024 International Conference on Antimicrobial Agents, position 2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a versatile scaffold for addressing emerging infectious diseases.

In conclusion, 2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 517920-59-1) represents a multifaceted tool in modern drug discovery and development. Its applications span from synthetic chemistry to clinical therapeutics, with recent breakthroughs in proteasome inhibition, diagnostic imaging, and antiviral therapy. As research continues to uncover new applications and optimize its properties, this compound is poised to play an increasingly important role in addressing unmet medical needs across multiple disease areas.

• 87100-28-5(Benzylboronic acid pinacol ester)
• 356570-52-0(4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane)
• 1379610-55-5(4,4,5,5-Tetramethyl-2-(naphthalen-2-ylmethyl)-1,3,2-dioxaborolane)
• 121074-61-1(1,3-Dioxolane,4,4,5,5-tetramethyl-2-(phenylmethyl)-)
• 1138077-59-4(2-(1-(3-chlorophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 475250-57-8(4,4,5,5-Tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane)
• 475250-49-8(2-[(4-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 390381-02-9(4,4,5,5-tetramethyl-2-(o-tolylmethyl)-1,3,2-dioxaborolane)
• 850567-54-3(1-(4-Chlorophenyl)vinylboronic acid, pinacol ester)
• 444094-88-6(2-(4-Chlorophenyl)ethylboronic acid pinacol ester)