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

Research Brief on Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 269410-00-6) in Chemical Biology and Pharmaceutical Applications

Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 269410-00-6) is a boronic ester derivative that has garnered significant attention in chemical biology and pharmaceutical research due to its versatile applications in Suzuki-Miyaura cross-coupling reactions and as a key intermediate in the synthesis of bioactive molecules. Recent studies have highlighted its role in the development of novel therapeutic agents, particularly in oncology and inflammation-related diseases. This research brief synthesizes the latest findings on this compound, focusing on its synthetic utility, biological activity, and potential clinical applications.

Recent advancements in the synthesis of Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate have demonstrated improved yields and purity through optimized catalytic systems and reaction conditions. A 2023 study published in the Journal of Medicinal Chemistry reported a novel palladium-catalyzed protocol that achieves >90% yield with minimal byproducts, enhancing its scalability for industrial applications. The compound's stability under physiological conditions has also been investigated, with findings suggesting its suitability for prodrug design and targeted drug delivery systems.

In the context of drug discovery, Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate has emerged as a crucial building block for boron-containing pharmaceuticals. Its incorporation into proteasome inhibitors and kinase-targeted therapies has shown promising results in preclinical models. For instance, derivatives of this compound have exhibited potent inhibitory activity against BTK (Bruton's tyrosine kinase) in B-cell malignancies, with IC50 values in the nanomolar range. Structural-activity relationship (SAR) studies have further elucidated the importance of the boronic ester moiety for target engagement and selectivity.

The compound's role in PET (positron emission tomography) tracer development has also been explored, leveraging the boron atom for isotopic labeling. Research teams have successfully synthesized ¹⁸F-labeled analogs of Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate for imaging applications in oncology, demonstrating high tumor uptake and favorable pharmacokinetics in murine models. These developments underscore the compound's dual utility as both a therapeutic agent and a diagnostic tool.

From a safety and toxicology perspective, recent in vitro and in vivo studies have provided valuable insights into the compound's metabolic profile. Hepatocyte assays indicate that the ethyl ester moiety undergoes rapid hydrolysis, while the boronic acid derivative shows moderate plasma protein binding. These findings have important implications for dosage optimization and formulation strategies in clinical development.

Looking ahead, the pharmaceutical industry is increasingly recognizing the potential of Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate as a versatile scaffold for next-generation therapeutics. Ongoing research is focusing on its application in targeted protein degradation (PROTACs) and as a component of antibody-drug conjugates (ADCs). With several derivatives currently in preclinical development pipelines, this compound class is poised to make significant contributions to precision medicine in the coming years.

• 171364-80-0(Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 480425-35-2(methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 903895-48-7(3-t-Butoxycarbonylphenylboronic acid, pinacol ester)
• 1218791-30-0(3-(Isopropoxycarbonyl)-5-methylphenylboronic acid, pinacol ester)
• 17136-80-0(METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE)
• 195062-62-5(4-Ethoxycarbonylphenylboronic acid, pinacol ester)
• 562098-07-1(3-Acetoxymethylphenylboronic acid, pinacol ester)
• 850568-72-8(Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 929626-17-5(Methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)
• 1150271-63-8(3-(Ethoxycarbonyl)-5-methylphenylboronic Acid Pinacol Ester)