518070-19-4 | 3-FLUORO-5-METHYLBENZOIC ACID

CAS:518070-19-4 | 3-FLUORO-5-METHYLBENZOIC ACID,Description

3-Fluoro-5-methylbenzoic acid is a compound that belongs to the class of organic compounds known as fluorobenzoic acids. These are compounds containing a benzene ring substituted with one fluorine and a carboxylic acid group. Although the provided papers do not directly discuss 3-fluoro-5-methylbenzoic acid, they do provide insights into similar fluorinated benzoic acid derivatives and their chemical behavior, which can be extrapolated to understand the properties and potential reactivity of 3-fluoro-5-methylbenzoic acid.

Synthesis Analysis

The synthesis of fluorinated benzoic acid derivatives often involves halogenation, nitration, esterification, and other reactions that introduce or modify functional groups on the benzene ring. For example, the synthesis of 3-chloro-2,4-difluoro-5-hydroxybenzoic acid from 2,4-difluoro-3-chlorobenzoic acid involves a series of reactions including nitration, esterification, and hydrolysis. Similarly, the synthesis of methyl 2-amino-5-fluorobenzoate from 3-fluorobenzoic acid involves nitrification, esterification, and reduction. These methods could potentially be adapted for the synthesis of 3-fluoro-5-methylbenzoic acid by starting with appropriate fluorinated benzoic acid precursors and introducing a methyl group at the correct position.

Molecular Structure Analysis

The molecular structure of fluorinated benzoic acids is characterized by the presence of strong electron-withdrawing fluorine atoms, which can influence the electronic distribution in the benzene ring and affect the acidity of the carboxylic acid group. In the case of 3-fluorobenzoylaminophenyl 3-fluorobenzoate, the molecular structure is stabilized by a combination of strong N-H...O hydrogen bonds and weak C-H...F interactions. These types of interactions are likely to be present in 3-fluoro-5-methylbenzoic acid as well, affecting its crystalline structure and physical properties.

Chemical Reactions Analysis

Fluorinated benzoic acids can participate in various chemical reactions, often serving as building blocks for more complex molecules. For instance, 4-chloro-2-fluoro-5-nitrobenzoic acid is used as a multireactive building block for the synthesis of various heterocyclic compounds. The presence of fluorine can also enhance the reactivity of other substituents on the benzene ring, as seen in the synthesis of lanthanide complexes with 2-fluorobenzoic acid. These examples suggest that 3-fluoro-5-methylbenzoic acid could also be used in the synthesis of heterocyclic compounds and coordination complexes.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated benzoic acids are influenced by the presence of fluorine, which is highly electronegative and can affect the acidity, boiling point, and solubility of the compound. For example, the solvatomorphism observed in 3-fluorobenzoylaminophenyl 3-fluorobenzoate is a result of the interplay between hydrogen bonds and weak intermolecular interactions involving fluorine. The fluorine atoms in 3-fluoro-5-methylbenzoic acid are expected to similarly influence its physical properties, such as melting point and solubility, as well as its chemical reactivity.

Scientific Research Applications

Biodegradation and Environmental Applications

• Methanogenic Degradation of Aromatic Compounds : A study highlighted the use of fluorinated compounds like 6-Fluoro-3-methylphenol in understanding the degradation pathway of m-cresol in a methanogenic consortium. The research suggested a novel demethylation step, which could facilitate the transformation of the methyl group to methane (Londry & Fedorak, 1993).

Chemical Synthesis and Material Science

• Synthesis of Organic Intermediates : Research on the synthesis of 3-borono-5-fluorobenzoic acid, an important intermediate in organic synthesis, was noted. This compound is used in the Suzuki aryl-coupling reaction for synthesizing olefins, styrenes, and biphenyl derivatives (Sun Hai-xia et al., 2015).
• Synthesis of Pharmaceutical Intermediates : A study described the synthesis of Methyl 2-amino-5-fluorobenzoate using 3-fluorobenzoic acid as raw material. This process is relevant in pharmaceutical applications (Yin Jian-zhong, 2010).

Biological and Pharmaceutical Research

• Fluorescent Sensors : A study developed a fluorogenic chemosensor using compounds related to 3-Fluoro-5-methylbenzoic acid. This sensor showed high selectivity and sensitivity toward aluminum ions, with potential applications in bio-imaging (Xingpei Ye et al., 2014).

Safety And Hazards

3-Fluoro-5-methylbenzoic acid may cause skin irritation, serious eye irritation, and respiratory irritation. It should be handled in a well-ventilated place with suitable protective clothing.

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