182344-16-7 | 4-FLUORO-2-(TRIFLUOROMETHYL)BENZENEBORONIC ACID

CAS:182344-16-7 | 4-FLUORO-2-(TRIFLUOROMETHYL)BENZENEBORONIC ACID,Description

(4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid is a boronic acid derivative with significant importance in organic synthesis and materials science. It is particularly noted for its role in the Suzuki-Miyaura cross-coupling reactions, which are pivotal in creating biaryl motifs commonly found in pharmaceuticals, agrochemicals, and organic materials.

Synthesis Analysis

The synthesis of related boronic acids involves lithiation of aromatic compounds followed by a reaction with boron trihalides or trialkyl borates. Specific methodologies can vary depending on the substituents present on the aromatic ring and the desired boronic acid product. For example, Das et al. reported the synthesis of amino-3-fluorophenyl boronic acid from 4-bromo-2-fluoroaniline through a series of protection, lithiation, and borylation steps, indicating similar synthetic routes may be applicable for (4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid (Das et al., 2003).

Molecular Structure Analysis

The molecular structure of boronic acids is characterized by the boron atom bonded to two hydroxyl groups and an aromatic moiety. In the case of fluoro-substituted phenylboronic acids, fluorine atoms influence the electronic structure and geometry of the molecule due to their electronegativity and steric effects. Crystallographic studies, such as those by Madura et al., can provide insights into the hydrogen bonding and supramolecular organization influenced by fluoro substitutions (Madura et al., 2014).

Chemical Reactions and Properties

Boronic acids participate in several types of chemical reactions, most notably in Suzuki-Miyaura cross-coupling to form C-C bonds. The presence of fluorine atoms can affect the reactivity and selectivity of these reactions. For example, research by Kinzel et al. has shown that certain boronic acids can undergo fast Suzuki-Miyaura coupling reactions under optimized conditions, suggesting that the fluorinated phenylboronic acids could exhibit similar reactivity patterns (Kinzel et al., 2010).

Scientific Research Applications

• Fluorescence Quenching Studies : Boronic acid derivatives, including similar compounds like 4-fluoro-2-methoxyphenyl boronic acid, have been studied for their fluorescence quenching properties. These studies are important in understanding the interaction of these compounds with other molecules and have potential applications in analytical chemistry (Geethanjali et al., 2015).
• Polymer Science : This compound has been used in synthesizing high glass-transition temperature and organosoluble arylene ether polymers. These polymers show outstanding thermal stability and could be used in various applications requiring materials with high-temperature resistance (Huang et al., 2007).
• Optical Modulation in Nanotechnology : Phenyl boronic acids, including similar structures, have been used to modify the optical properties of single-walled carbon nanotubes. This research has implications in the development of sensors and other nanotechnology applications (Mu et al., 2012).
• Catalysis in Organic Synthesis : Compounds like 2,4-bis(trifluoromethyl)phenylboronic acid have shown efficacy as catalysts in dehydrative condensation, which is a key reaction in organic synthesis (Wang et al., 2018).
• Chemical Sensing and Binding : Studies have shown that boronic acid derivatives, similar to (4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid, can interact with sugars, indicating potential applications in chemical sensing and molecular recognition (Bhavya et al., 2016).
• Diagnostic Imaging in Medicine : This compound has been used in the synthesis of radiotracers for positron emission tomography (PET) imaging, particularly in boron neutron capture therapy-oriented diagnosis (Ishiwata et al., 2018).

Safety And Hazards

This compound is considered hazardous by the 2012 OSHA Hazard Communication Standard. It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray and to use only outdoors or in a well-ventilated area.

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