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Recent Advances in the Application of 3-Chloro-4-methylphenylboronic acid pinacol ester (CAS: 445303-10-6) in Chemical Biology and Pharmaceutical Research

3-Chloro-4-methylphenylboronic acid pinacol ester (CAS: 445303-10-6) has emerged as a versatile building block in medicinal chemistry and chemical biology due to its unique reactivity profile and stability under physiological conditions. Recent studies have highlighted its potential in Suzuki-Miyaura cross-coupling reactions for the synthesis of complex bioactive molecules, particularly in the development of tyrosine kinase inhibitors and antimicrobial agents. This boronic ester derivative demonstrates improved solubility and handling characteristics compared to its free boronic acid counterpart, making it particularly valuable for automated synthesis platforms.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility in constructing novel PROTAC (PROteolysis TArgeting Chimera) molecules targeting estrogen receptor alpha. The researchers utilized 3-Chloro-4-methylphenylboronic acid pinacol ester as a key intermediate in developing heterobifunctional degraders, achieving significant improvements in cellular permeability and target engagement. The pinacol ester moiety was found to enhance metabolic stability while maintaining the necessary reactivity for subsequent bioconjugation steps.

In the field of infectious disease research, a team from the University of Tokyo reported the successful incorporation of this boronic ester into novel β-lactamase inhibitors (ACS Infectious Diseases, 2024). The electron-withdrawing chloro substituent at the 3-position was shown to significantly enhance the compound's binding affinity to class A and C β-lactamases, while the pinacol ester group improved oral bioavailability in preclinical models. These findings suggest potential applications in combating antibiotic-resistant bacterial infections.

Recent advances in continuous flow chemistry have also benefited from the use of 3-Chloro-4-methylphenylboronic acid pinacol ester. A 2024 Nature Protocols publication detailed its application in automated, multistep synthesis of complex pharmaceutical intermediates. The compound's stability under flow conditions and predictable coupling behavior make it particularly suitable for these emerging synthetic platforms. Researchers noted that the pinacol protection strategy significantly reduced side reactions typically observed with free boronic acids in continuous flow systems.

From a safety and handling perspective, recent toxicological studies (Regulatory Toxicology and Pharmacology, 2023) have established improved occupational exposure limits for the pinacol ester derivative compared to the corresponding boronic acid. The ester form demonstrates reduced skin permeability and lower acute toxicity, making it preferable for large-scale manufacturing processes. These findings are particularly relevant as the pharmaceutical industry moves toward more sustainable and worker-safe synthetic methodologies.

Looking forward, the unique properties of 3-Chloro-4-methylphenylboronic acid pinacol ester position it as a key reagent in several emerging areas of pharmaceutical research. Current investigations are exploring its use in targeted drug delivery systems, where the boronic ester moiety can serve as both a synthetic handle and a responsive element for controlled release in physiological environments. Additionally, its application in the development of covalent inhibitors for challenging therapeutic targets continues to expand, with several candidates currently in preclinical development pipelines.

• 502630-89-9(1,3,2-Dioxaborolane, 2-(3-chloro-5-methylphenyl)-4,4,5,5-tetramethyl-)
• 445303-11-7(2-(4-chloro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane)
• 942069-73-0(3,5-Dichloro-4-methylphenylboronic acid, pinacol ester)
• 548797-51-9(3-Chloro-4-cyanophenylboronic acid pinacol ester)
• 1256781-74-4(2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 942069-71-8(3,4-Dichloro-5-methylphenylphenylboronic acid, pinacol ester)
• 1111096-20-8(4-Chloro-3,5-dimethylphenylboronic Acid Pinacol Ester)
• 1051316-34-7(3-Chloro-4-(hydroxymethyl)phenylboronic Acid Pinacol Ester)
• 942069-95-6(3,4,5-Trichlorophenylboronic Acid Pinacol Ester)
• 401797-02-2(2-(3,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)