179899-07-1 | 4-Fluoro-2-methoxyphenylboronic acid

CAS:179899-07-1 | 4-Fluoro-2-methoxyphenylboronic acid,Description

Synthesis Analysis

The synthesis of related fluorophenylboronic acids involves complex chemical reactions. For instance, the synthesis of a compound with a similar structure, involving fluoro, methoxy, and phenyl groups, was achieved through a multi-step process, including O-methylation and subsequent Schiff reaction, demonstrating the complexity and specificity required in synthesizing such molecules (Vos & Slegers, 1994) .

Molecular Structure Analysis

The molecular structure of fluorinated phenylboronic acids has been thoroughly investigated, revealing the impact of fluorine substituents on the compound's properties. For example, studies on isomeric fluoro-2-formylphenylboronic acids provided insights into how the fluorine position affects molecular and crystal structures, showcasing the significance of molecular structure analysis in understanding the behavior of such compounds (Kowalska et al., 2016).

Chemical Reactions and Properties

Fluorophenylboronic acids participate in various chemical reactions, highlighting their reactivity and utility in organic synthesis. For instance, their use in cross-coupling reactions as coupling partners has been demonstrated, showing the versatility and efficiency of these compounds in forming complex organic molecules (Chen et al., 2016).

Physical Properties Analysis

The physical properties of fluorophenylboronic acids, such as stability and fluorescence, have been the subject of research. A study on a novel fluorophore related to this class of compounds revealed strong fluorescence and stability across a wide pH range, indicating the potential of fluorophenylboronic acids in applications requiring stable, fluorescent materials (Hirano et al., 2004).

Chemical Properties Analysis

The chemical behavior of 4-Fluoro-2-methoxyphenylboronic acid, particularly its reactivity in boronic acid-based reactions, is of great interest. Research has shown that the presence of fluorine and methoxy groups can significantly influence the reactivity and outcomes of chemical reactions involving boronic acids, leading to the selective synthesis of complex organic structures (Xiong et al., 2019).

Scientific Research Applications

• Suzuki-Miyaura Cross-Coupling Reactions

  • Application : This compound is used as a reactant in Suzuki-Miyaura cross-coupling reactions, which are used to synthesize various organic compounds.
  • Results : The outcome of these reactions is the formation of new carbon-carbon bonds, which is a key step in the synthesis of many organic compounds.

• Synthesis of Biologically Active Molecules

  • Application : 4-Fluoro-2-methoxyphenylboronic acid is used as a reactant or precursor in the synthesis of biologically active molecules, including GSK-3β inhibitors.
  • Results : The results can also vary, but in the case of GSK-3β inhibitors, these compounds have potential therapeutic applications in a range of diseases, including neurodegenerative disorders, type 2 diabetes, and cancer.

• Synthesis of Heterobiaryls

  • Application : This compound is used in Suzuki-Miyaura cross-coupling reactions for the synthesis of heterobiaryls.
  • Results : The outcome of these reactions is the formation of new carbon-carbon bonds, which is a key step in the synthesis of many organic compounds.

• Synthesis of Antithrombotic Drugs

  • Application : 4-Fluoro-2-methoxyphenylboronic acid is used in Suzuki and Still coupling for the synthesis of antithrombotic drugs.
  • Results : The results can also vary, but in the case of antithrombotic drugs, these compounds have potential therapeutic applications in a range of diseases.

• Electrochemical Redox Probe

  • Application : While this specific application is not for 4-Fluoro-2-methoxyphenylboronic acid, but for a similar compound, 4-Methoxyphenylboronic acid, it’s worth mentioning that boronic acids can be used as electrochemical redox probes for the selective detection of hydrogen peroxide (H2O2) in live cells.
  • Results : The outcome of these reactions is the selective detection of hydrogen peroxide, which is a key molecule in various biological processes.

• Chemical Vapor Deposition (CVD) of Graphene

  • Application : Again, this is an application of 4-Methoxyphenylboronic acid, but it illustrates the versatility of boronic acids. It is used in the chemical vapor deposition (CVD) of graphene with in-situ phosphorous or boron doping.
  • Results : The outcome is the formation of doped graphene, which has unique properties and potential applications in various fields.

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard. It is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation.

Future Directions

The introduction of a boronic acid group to bioactive molecules has shown to modify selectivity, physicochemical, and pharmacokinetic characteristics, improving the already existing activities. This suggests that further studies with boronic acids, including 4-Fluoro-2-methoxyphenylboronic acid, could lead to the development of new promising drugs.

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