871329-52-1 | 2-Chloro-3-fluorophenylboronic acid

CAS:871329-52-1 | 2-Chloro-3-fluorophenylboronic acid,Description

2-Chloro-3-fluorophenylboronic acid is a boronic acid derivative that is part of a broader class of organoboron compounds which are widely used in organic synthesis and medicinal chemistry. While the specific compound is not directly discussed in the provided papers, the general behavior and reactivity of similar boronic acids are well-documented. These compounds are known for their versatility in cross-coupling reactions, such as the Suzuki-Miyaura coupling, and their ability to form stable complexes with various substrates.

Synthesis Analysis

The synthesis of boronic acids often involves the use of halogenated aromatic compounds as starting materials. For instance, the synthesis of 2-fluoro-4-(trans-4-alkylcyclohexyl)phenylboronic acid was achieved using a halogenated benzene derivative, n-butyllithium, tributyl borate, and potassium tert-butoxide, with the reaction conditions optimized for yield and reaction time. Although the specific synthesis of 2-chloro-3-fluorophenylboronic acid is not detailed, similar methodologies could be applied, adjusting the reactants and conditions to accommodate the chloro and fluoro substituents.

Molecular Structure Analysis

The molecular structure of boronic acids can vary depending on their substituents and the environment. X-ray diffraction studies have revealed diverse solid-state molecular structures ranging from planar open forms to twisted conformers and cyclic oxaborole derivatives. The presence of halogen substituents, such as fluorine, can influence the molecular geometry and the stability of these compounds.

Chemical Reactions Analysis

Boronic acids participate in a variety of chemical reactions. They are known to undergo tautomeric rearrangements, as seen with functionalized 2-formylphenylboronic acids forming 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles. Additionally, they can catalyze dehydrative condensation reactionsand engage in cascade reactions involving the formation of multiple bonds, as demonstrated by the synthesis of benzofuro[2,3-c]pyridines. The reactivity can be further tuned by the nature of the substituents, which can either facilitate or inhibit certain reaction pathways.

Physical and Chemical Properties Analysis

The physical and chemical properties of boronic acids are influenced by their substituents. For example, the pKa values, which are indicative of acidity, can be affected by the presence of fluorine atoms. The tautomeric equilibrium between the boronic acid and benzoxaborole forms is also a key feature, with implications for the compound's stability and reactivity. The antifungal activity of some formylphenylboronic acids suggests potential biological applications, which could extend to 2-chloro-3-fluorophenylboronic acid by analogy.

Scientific Research Applications

Synthesis and Transformation

A study by Szumigala et al. (2004) developed a scalable synthesis of 2-bromo-3-fluorobenzonitrile via bromodeboronation of 2-cyano-6-fluorophenylboronic acid, demonstrating the generality of this transformation through halodeboronation of various aryl boronic acids, including 2-chloro-3-fluorophenylboronic acid (Szumigala et al., 2004).

Spectroscopic Analysis

Erdoğdu et al. (2009) conducted detailed experimental and theoretical vibrational spectra studies of 2-fluorophenylboronic acid, a related compound, which provides insights into the spectroscopic characteristics of 2-chloro-3-fluorophenylboronic acid derivatives (Erdoğdu et al., 2009) .

Fluorescence Quenching Studies

Geethanjali et al. (2015) explored the fluorescence quenching mechanisms in boronic acid derivatives, including 2-chloro-3-fluorophenylboronic acid, providing insights into their photophysical properties (Geethanjali et al., 2015).

Suzuki Cross-Coupling Reaction

Ikram et al. (2015) reported the synthesis of various thiophene derivatives via a palladium-catalyzed Suzuki cross-coupling reaction using arylboronic acids including 2-chloro-3-fluorophenylboronic acid, highlighting its utility in forming biologically active compounds (Ikram et al., 2015).

Adsorption Mechanism Studies

Piergies et al. (2013) conducted systematic spectroscopic studies on the adsorption mechanisms of various phenylboronic acids, which can be extrapolated to understand the behavior of 2-chloro-3-fluorophenylboronic acid on surfaces (Piergies et al., 2013).

Educational Applications

Lee et al. (2020) introduced an undergraduate laboratory experiment involving the Suzuki–Miyaura cross coupling of 4-fluorophenylboronic acid, which can be related to the use of 2-chloro-3-fluorophenylboronic acid in educational settings (Lee et al., 2020).

Antifungal Activity Studies

Borys et al. (2019) found that 2-formylphenylboronic acid and its fluoro analogs exhibit antifungal activity, which may be relevant to the antifungal properties of 2-chloro-3-fluorophenylboronic acid (Borys et al., 2019).

Microwave-Assisted Synthesis

Cailly et al. (2006) utilized microwave-assisted Suzuki cross-coupling reactions involving 2-fluorophenylboronic acid, demonstrating a method that could be applicable to 2-chloro-3-fluorophenylboronic acid (Cailly et al., 2006).

MRI Probe Development

Nonaka et al. (2015) reported on a 2-fluorophenylboronic acid-based MRI probe for hydrogen peroxide detection, which might inform similar applications for 2-chloro-3-fluorophenylboronic acid (Nonaka et al., 2015).

Safety And Hazards

2-Chloro-3-fluorophenylboronic acid may cause respiratory irritation, is harmful if swallowed, causes serious eye irritation, and causes skin irritation. Precautions should be taken to avoid breathing dust/fume/gas/mist/vapours/spray, and protective gloves/protective clothing/eye protection/face protection should be worn.

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