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4-Bromo-2-ethoxyphenylboronic acid (CAS No. 2096329-53-0): A Versatile Boronic Acid Derivative in Modern Organic Synthesis

4-Bromo-2-ethoxyphenylboronic acid (CAS No. 2096329-53-0) is a highly specialized boronic acid derivative that has gained significant attention in pharmaceutical and materials science research. This compound, characterized by its unique bromo and ethoxy functional groups, serves as a critical building block in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern C-C bond formation strategies. Its molecular structure, C8H10BBrO3, offers exceptional reactivity while maintaining stability under controlled conditions.

In recent years, the demand for 4-Bromo-2-ethoxyphenylboronic acid has surged due to its applications in drug discovery and agrochemical development. Researchers particularly value its role in constructing biaryl motifs, which are prevalent in FDA-approved drugs and biologically active compounds. The ethoxy group enhances solubility in organic solvents, while the bromo substituent provides a handle for further functionalization, making it a multifunctional synthetic intermediate.

The compound's significance extends to material science, where it contributes to the synthesis of organic electronic materials and liquid crystal displays (LCDs). Its ability to participate in palladium-catalyzed reactions aligns with the growing trend toward green chemistry and atom-efficient synthesis. Industry professionals frequently search for "4-Bromo-2-ethoxyphenylboronic acid solubility" or "CAS 2096329-53-0 storage conditions," reflecting practical concerns about handling this air-sensitive reagent.

From a structural-activity relationship perspective, the ortho-ethoxy configuration in 4-Bromo-2-ethoxyphenylboronic acid influences its steric hindrance and electronic properties, factors crucial for catalyst turnover in coupling reactions. Recent publications highlight its use in developing kinase inhibitors and antiviral agents, addressing global health challenges. The compound's crystalline form (often white to off-white powder) and high purity grade (>97%) make it suitable for high-throughput screening applications.

Quality control of CAS 2096329-53-0 typically involves HPLC analysis and 1H/13C NMR verification, ensuring batch-to-batch consistency for sensitive reactions. Suppliers often provide technical data sheets detailing its melting point (≈150-155°C) and optimal storage temperature (2-8°C under inert atmosphere). These specifications respond to frequent queries like "how to stabilize boronic acids" or "2096329-53-0 shelf life" from synthetic chemists.

Emerging applications include its incorporation into MOFs (Metal-Organic Frameworks) and covalent organic polymers for gas storage. The compound's boron center enables dynamic covalent chemistry, a hot topic in smart material design. Environmental considerations drive interest in its biodegradation pathways and ecotoxicity profile, particularly for industrial-scale use.

For laboratory handling, 4-Bromo-2-ethoxyphenylboronic acid requires anhydrous conditions to prevent hydrolysis of the boronic acid moiety. This aligns with search trends for "handling moisture-sensitive reagents" and "Schlenk technique for boronic acids." Its compatibility with microwave-assisted synthesis further enhances its utility in accelerated reaction optimization.

Patent analysis reveals growing IP activity around 2096329-53-0 derivatives, particularly in photoredox catalysis and borylation reactions. The compound's molecular weight (245.88 g/mol) and logP value (~2.3) make it favorable for medicinal chemistry applications requiring balanced lipophilicity. These properties address common search queries about "boronic acid drug permeability" in ADME studies.

In conclusion, 4-Bromo-2-ethoxyphenylboronic acid (CAS 2096329-53-0) represents a strategic intersection of synthetic utility and molecular diversity. Its evolving applications across life sciences and advanced materials ensure its continued relevance in cutting-edge research, answering the scientific community's need for high-performance building blocks.

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