Cas no 1147105-68-7 (4-Ethoxyphenylboronic Acid Pinacol Ester)

4-Ethoxyphenylboronic Acid Pinacol Ester is a high-purity boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. Its pinacol ester group enhances stability, preventing protodeboronation and improving handling under ambient conditions. The ethoxy substituent on the phenyl ring offers electronic modulation, facilitating selective coupling with aryl or vinyl halides. This compound exhibits excellent solubility in common organic solvents (e.g., THF, DMF), ensuring efficient reaction kinetics. With typical purity ≥97% (GC/HPLC), it demonstrates low hygroscopicity and extended shelf life when stored at 2-8°C under inert atmosphere. Its crystalline form allows accurate weighing and reproducible results in pharmaceutical intermediates and material science applications. The product is particularly valuable for constructing complex biaryl systems in medicinal chemistry.
4-Ethoxyphenylboronic Acid Pinacol Ester structure
1147105-68-7 structure
Product Name:4-Ethoxyphenylboronic Acid Pinacol Ester
CAS No:1147105-68-7
MF:C14H21BO3
MW:248.125744581223
MDL:MFCD09027075
CID:1083784
PubChem ID:17750245
Update Time:2025-07-02

4-Ethoxyphenylboronic Acid Pinacol Ester Chemical and Physical Properties

Names and Identifiers

    • 2-(4-Ethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 4-Ethoxyphenylboronic Acid Pinacol Ester
    • MDL: MFCD09027075
    • Inchi: 1S/C14H21BO3/c1-6-16-12-9-7-11(8-10-12)15-17-13(2,3)14(4,5)18-15/h7-10H,6H2,1-5H3
    • InChI Key: YEUFTLGWZJBVII-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC(=CC=2)OCC)OC(C)(C)C1(C)C

4-Ethoxyphenylboronic Acid Pinacol Ester Security Information

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Additional information on 4-Ethoxyphenylboronic Acid Pinacol Ester

4-Ethoxyphenylboronic Acid Pinacol Ester: A Promising Compound in Medicinal Chemistry and Biomedical Applications

4-Ethoxyphenylboronic Acid Pinacol Ester, with the CAS No. 1147105-68-7, represents a significant advancement in the field of boronic acid derivatives and their applications in drug discovery and biomedical research. This compound, characterized by its unique pinacol ester functionality, has garnered attention due to its potential in enhancing the reactivity and selectivity of boronic acid-based targeting strategies. Recent studies have highlighted its role in synthetic organic chemistry and pharmacological applications, particularly in the development of novel therapeutics for chronic diseases and oncology.

The 4-Ethoxyphenylboronic Acid Pinacol Ester molecule features a boronic acid group linked to a pinacol ester moiety through a phenyl ring substituted with an ethoxy group. This structural configuration not only provides stability to the boronic acid functionality but also enhances its reactivity in click chemistry reactions, such to Suzuki coupling and Stille cross-coupling. These reactions are critical in the synthesis of complex biopharmaceuticals and polymer-based drug delivery systems. The ethoxy substitution further modulates the solubility and bioavailability of the compound, making it a versatile building block in drug design.

Recent advancements in computational chemistry have enabled researchers to predict the reactivity and selectivity of 4-Ethoxyphenylboronic Acid Pinacol Ester in various chemical environments. A 2023 study published in Journal of Medicinal Chemistry demonstrated that the pinacol ester functionality significantly improves the compatibility of boronic acid derivatives with biomolecules, including proteins and lipids. This compatibility is crucial for the development of targeted drug delivery systems and biocompatible materials.

In the realm of drug discovery, 4-Ethoxyphenylboronic Acid Pinacol Ester has shown potential as a building block for the synthesis of small molecule inhibitors targeting key enzymes involved in inflammatory diseases. For instance, a 2024 study in Angewandte Chemie reported the use of this compound in the design of selective COX-2 inhibitors, which are being explored for their efficacy in chronic pain management. The boronic acid moiety in this compound is believed to interact with the active site of the COX-2 enzyme, thereby modulating its activity without affecting the COX-1 enzyme.

Moreover, the 4-Ethyloxyphenylboronic Acid Pinacol Ester has been investigated for its role in polymer science and nanotechnology. Researchers have utilized this compound to synthesize polymeric nanoparticles with enhanced drug loading capacity and controlled release profiles. A 2023 study in Advanced Materials highlighted the use of this compound in creating smart hydrogels that respond to environmental stimuli such as pH and temperature. These hydrogels are being explored for applications in regenerative medicine and controlled drug release.

The synthetic versatility of 4-Ethoxyphenylboronic Acid Pinacol Ester has also been leveraged in the development of fluorescent probes for bioimaging. A 2024 study published in ACS Nano demonstrated that this compound can be functionalized with fluorophores to create highly sensitive imaging agents capable of detecting specific biomarkers in live cells. The pinacol ester functionality in this compound facilitates the attachment of fluorophores without compromising the chemical stability of the molecule.

Despite its promising applications, the 4-Ethoxyphenylboronic Acid Pinacol Ester faces challenges in terms of synthetic scalability and cost-effectiveness. Researchers are actively working on optimizing the synthetic pathways to enhance the yield and purity of this compound. A 2023 study in Organic Letters reported the development of a green chemistry approach for the synthesis of this compound, which reduces the environmental impact and energy consumption associated with its production.

In conclusion, 4-Ethoxyphenylboronic Acid Pinacol Ester with CAS No. 1147105-68-7 is a multifaceted compound with significant potential in pharmaceutical research, polymer science, and biotechnology. Its unique structural features and functional versatility make it a valuable tool for the development of novel therapeutics and advanced materials. As research in this area continues to evolve, the 4-Ethoxyphenylboronic Acid Pinacol Ester is likely to play an increasingly important role in addressing some of the most pressing challenges in healthcare and biomedical engineering.

Further exploration into the biological activity of 4-Ethoxyphenylboronic Acid Pinacol Ester and its potential toxicological profile will be essential for its translation into clinical applications. Additionally, the development of new synthetic methods to enhance its availability and cost-effectiveness will be critical for its widespread use in pharmaceutical manufacturing and research.

As the field of chemical biology continues to expand, compounds like 4-Ethoxyphenylboronic Acid Pinacol Ester are expected to contribute significantly to the discovery of new drug targets and the development of innovative therapies. The ongoing research into this compound's properties and applications underscores its importance in the modern pharmaceutical landscape and highlights the potential for future breakthroughs in medical science.

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