946525-43-5 | 4-Difluoromethyl-phenylboronic acid

CAS:946525-43-5 | 4-Difluoromethyl-phenylboronic acid,Description

(4-(Difluoromethyl)phenyl)boronic acid is a boronic acid derivative that is part of a class of compounds known for their utility in organic synthesis and materials science. While the provided papers do not directly discuss this specific compound, they do provide insights into the general behavior and applications of boronic acids, which can be extrapolated to (4-(Difluoromethyl)phenyl)boronic acid.

Synthesis Analysis

The synthesis of boronic acid derivatives often involves halogen-lithium exchange reactions, followed by the addition of a borate ester and subsequent hydrolysis, as described for the synthesis of amino-3-fluorophenyl boronic acid. This method could potentially be adapted for the synthesis of (4-(Difluoromethyl)phenyl)boronic acid by starting with an appropriate halogenated precursor.

Molecular Structure Analysis

Boronic acids typically exhibit tetrahedral coordination at the boron center when bound to two oxygen atoms, as seen in the crystal structure of difluoro[2-(4-methoxyphenyl)-3-oxo-3-phenylpropanalato]boron(III). This suggests that (4-(Difluoromethyl)phenyl)boronic acid would also exhibit a tetrahedral geometry around the boron atom.

Chemical Reactions Analysis

Boronic acids are known to participate in various chemical reactions, including Suzuki cross-coupling, amidation, and complexation with diols. The presence of fluorine substituents on the phenyl ring can influence the reactivity and acidity of boronic acids, as seen in the study of fluorinated 1,2-phenylenediboronic acids.

Physical and Chemical Properties Analysis

The physical and chemical properties of boronic acids can be significantly affected by the presence of fluorine atoms and the boronic group. For instance, fluorination can enhance the stability of certain structures and influence acidity. The presence of difluoromethyl groups in (4-(Difluoromethyl)phenyl)boronic acid would likely contribute to its unique physical and chemical properties, potentially affecting its solubility, stability, and reactivity.

Scientific Research Applications

Optical Modulation

• Optical Modulation with Carbon Nanotubes : Phenyl boronic acids, including derivatives similar to (4-(Difluoromethyl)phenyl)boronic acid, have been used for saccharide recognition and to modulate the optical properties of carbon nanotubes. The study demonstrated the link between molecular structure and photoluminescence quantum yield, indicating potential applications in optical sensing technologies (Mu et al., 2012).

Catalysis

• Catalysis in Amidation Reactions : A study reported the use of a related boronic acid, 2,4-Bis(trifluoromethyl)phenylboronic acid, as an effective catalyst for dehydrative amidation between carboxylic acids and amines. This suggests potential applications of (4-(Difluoromethyl)phenyl)boronic acid in catalyzing similar chemical reactions (Wang, Lu, & Ishihara, 2018).

Carbohydrate Binding

• Carbohydrate-Binding Applications : Boronic acids, including (4-(Difluoromethyl)phenyl)boronic acid, have been identified for their ability to complex with glycopyranosides under physiologically relevant conditions. This opens avenues for their use in designing receptors and sensors for cell-surface glycoconjugates (Dowlut & Hall, 2006).

Biomedical Applications

• Biomedical Applications : Phenylboronic-acid-modified nanoparticles, which could include derivatives like (4-(Difluoromethyl)phenyl)boronic acid, have shown potential as antiviral therapeutics, specifically against Hepatitis C virus. This highlights the biomedical application possibilities of such compounds (Khanal et al., 2013).
• Polymeric Boronic Acids in Medicine : Research on boronic acid-containing polymers, possibly including (4-(Difluoromethyl)phenyl)boronic acid, indicates their value in various biomedical applications such as HIV, diabetes, and cancer treatment. Their unique reactivity and solubility make them suitable for new biomaterials development (Cambre & Sumerlin, 2011).

Sensing Applications

• Fluorescence Sensing : The introduction of (4-(Difluoromethyl)phenyl)boronic acid derivatives in sensing applications, especially for detecting ions like ferric and fluoride in living cells, demonstrates their potential as bioimaging reagents (Selvaraj et al., 2019).

Chemical Synthesis

• Synthesis of DNA Modified with Boronic Acid : The study explored the use of phenylboronic acid in the postsynthetic modification of oligonucleotides, indicating potential applications in saccharide detection and fluorescent DNA aptamers (Steinmeyer & Wagenknecht, 2018).

Analytical Chemistry

• Structural Analysis Using NMR Spectroscopy : Phenyl boronic acids' reactivity with diols was analyzed using 11B NMR spectroscopy, which could have implications in medical diagnostics and biochemistry, potentially applicable to (4-(Difluoromethyl)phenyl)boronic acid (Valenzuela et al., 2022).

Safety And Hazards

“(4-(Difluoromethyl)phenyl)boronic acid” is classified as dangerous with the signal word “Danger”. It has hazard statements H228-H302-H314-H412, indicating that it is flammable, harmful if swallowed, causes severe skin burns and eye damage, and is harmful to aquatic life with long-lasting effects. Precautionary measures include avoiding contact with skin and eyes, not breathing dust, and wearing suitable personal protective equipment.

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