259209-20-6 | 4-FLUORO-2-HYDROXYPHENYLBORONIC ACID

CAS:259209-20-6 | 4-FLUORO-2-HYDROXYPHENYLBORONIC ACID,Description

5-Fluoro-2-hydroxyphenylboronic acid is a boronic acid derivative that contains a fluorine atom and a hydroxyl group on the phenyl ring. While the specific compound is not directly discussed in the provided papers, related compounds with similar structures, such as fluoro-substituted formylphenylboronic acids and other boronic acid derivatives, have been synthesized and characterized for their properties and potential applications in various fields, including medicine and materials science.

Synthesis Analysis

The synthesis of related fluoro-substituted phenylboronic acids typically involves the use of cross-coupling reactions, such as the Suzuki–Miyaura coupling, which is a palladium-catalyzed cross-coupling reaction between aryl halides and boronic acids. The synthesis of these compounds can also involve the use of other halogenated precursors and subsequent functional group transformations.

Molecular Structure Analysis

The molecular structure of fluoro-substituted phenylboronic acids is characterized by the presence of a boronic acid group attached to a phenyl ring that is substituted with fluorine and other functional groups. The position of the fluorine substituent can significantly influence the properties of the compound, including its tautomeric equilibria and acidity. X-ray diffraction studies have been used to determine the solid-state structures of these compounds.

Chemical Reactions Analysis

Fluoro-substituted phenylboronic acids can participate in various chemical reactions, including tautomeric cyclization to form benzoxaboroles, which are cyclic structures containing a boron atom. These compounds can also undergo reactions with other organic substrates, leading to the formation of complex molecules with potential biological activity.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluoro-substituted phenylboronic acids, such as acidity (pKa values), are influenced by the electron-withdrawing effects of the fluorine atom and other substituents on the phenyl ring. These properties are crucial for their reactivity and potential applications. For example, the presence of an electron-withdrawing substituent like fluorine can increase the acidity of the boronic acid, making it more reactive in coupling reactions.

Relevant Case Studies

Several studies have explored the antimicrobial and antifungal activities of fluoro-substituted phenylboronic acids. For instance, 5-trifluoromethyl-2-formylphenylboronic acid has shown moderate action against Candida albicans and higher activity against Aspergillus niger, Escherichia coli, and Bacillus cereus. Another study found that 4-fluoro-2-formylphenylboronic acid exhibited potent antifungal activity against various fungal strains. These findings suggest that fluoro-substituted phenylboronic acids have potential as antimicrobial agents.

Scientific Research Applications

1. Fluorescence Quenching Mechanism

5-Fluoro-2-hydroxyphenylboronic acid and its derivatives are studied for their role in fluorescence quenching mechanisms. These mechanisms are important in analytical chemistry, particularly in the study of fluorescence properties of compounds and their interactions with other molecules (Geethanjali, Nagaraja, & Melavanki, 2015).

2. Antiproliferative Potential in Cancer Research

Boronic acid derivatives, including those similar to 5-Fluoro-2-hydroxyphenylboronic acid, have been evaluated for their antiproliferative activities in cancer research. They are considered promising for developing novel anticancer agents due to their ability to induce apoptosis and arrest the cell cycle in cancer cells (Psurski et al., 2018).

3. Antifungal Activity

Fluoro-substituted boronic acids, including compounds similar to 5-Fluoro-2-hydroxyphenylboronic acid, have shown effectiveness against various fungal strains. Their antifungal properties are being explored, particularly in the development of new antifungal agents (Borys et al., 2019).

4. Development of Biomedical Sensors

This compound has potential in the development of biomedical sensors, especially in glucose sensing. Its ability to interact with sugars makes it valuable in creating sensitive and selective sensors for biomedical applications (Huang et al., 2013).

5. Synthesis of Silicon-Containing Drugs

The derivatives of 5-Fluoro-2-hydroxyphenylboronic acid have been used as building blocks in the synthesis of silicon-containing drugs. These compounds show promise in various pharmacological applications, including antimicrobial and antithrombolytic activities (Troegel et al., 2009).

6. Applications in Electrochemistry

Compounds similar to 5-Fluoro-2-hydroxyphenylboronic acid have been investigated for their electrochemical properties, particularly in the synthesis of charge storage materials and in electrochemical sensors (Wang et al., 2019).

7. Application in Molecular Imaging

5-Fluoro-2-hydroxyphenylboronic acid derivatives have been synthesized for potential use in molecular imaging, specifically as radioligands targeting certain brain receptors. This application is significant in the field of neurology and pharmaceutical research (Vos & Slegers, 1994) .

8. Organometallic Chemistry and Catalysis

It is utilized in organometallic chemistry, particularly in C-H silylation reactions. This compound serves as a directing agent in such reactions, influencing the regioselectivity and efficiency of the catalytic process (Ihara & Suginome, 2009).

Safety And Hazards

Safety data indicates that 5-Fluoro-2-hydroxyphenylboronic acid may cause skin and eye irritation. It is recommended to avoid dust formation, breathing mist, gas or vapours, and contact with skin and eyes. Use of personal protective equipment, including chemical impermeable gloves, is advised.

More Information