203302-97-0 | 3-Trifluoromethoxyphenylacetic acid

CAS:203302-97-0 | 3-Trifluoromethoxyphenylacetic acid,Description

3-(Trifluoromethoxy)phenylacetic acid is a compound that is structurally related to various fluorinated phenylacetic acid derivatives. These compounds are of interest due to their diverse range of applications, including their use in chromatographic separation techniques, spectroscopic analysis, and potential antibacterial properties. The trifluoromethoxy group (-OCF3) is particularly noteworthy for its influence on the acidity and reactivity of the phenylboronic acids in which it is incorporated .

Synthesis Analysis

The synthesis of trifluoromethyl-substituted phenylacetic acids can be achieved through various methods. One approach involves the use of phenyliodine(III) bis(trifluoroacetate) (PIFA), which promotes C-C coupling reactions leading to the formation of compounds with trifluoromethyl groups . Additionally, the photodecarboxylation of CF3-substituted phenylacetic acids has been shown to be an efficient method for generating trifluoromethyltoluenes, which are structurally related to 3-(trifluoromethoxy)phenylacetic acid .

Molecular Structure Analysis

The molecular structure of compounds related to 3-(trifluoromethoxy)phenylacetic acid has been studied using various spectroscopic techniques. For instance, NMR spectroscopy has been employed to characterize the structural and physicochemical properties of (trifluoromethoxy)phenylboronic acids . The introduction of the trifluoromethoxy group significantly affects the acidity and molecular structure, with the ortho isomer displaying a unique intramolecular hydrogen bond .

Chemical Reactions Analysis

The chemical reactivity of trifluoromethyl-substituted phenylacetic acids includes their ability to undergo photodecarboxylation, leading to the formation of benzylic carbanions that react with water . Additionally, the presence of the trifluoromethyl group can facilitate the determination of enantiomeric purity of chiral acids by conversion to their corresponding diastereomeric amides, as studied with α-amino-α-trifluoromethyl-phenylacetonitrile .

Physical and Chemical Properties Analysis

The physical and chemical properties of 3-(trifluoromethoxy)phenylacetic acid derivatives can be analyzed using chromatographic and spectrophotometric methods. Chromatographic separation techniques, such as high-performance liquid chromatography (HPLC), have been utilized to separate and detect various fluorinated phenylacetic acid isomers . Spectrophotofluorometric analysis has also been developed for the sensitive detection of related compounds in biological samples . The trifluoromethoxy group's impact on the acidity and reactivity of these compounds is significant, as it can influence their separation mechanisms and detection limits .

Scientific Research Applications

Antibacterial Properties

One significant application of compounds related to 3-(Trifluoromethoxy)phenylacetic Acid is in the field of antibacterial research. A study by Adamczyk-Woźniak et al. (2021) explored various isomers of (trifluoromethoxy)phenylboronic acids, closely related to 3-(Trifluoromethoxy)phenylacetic Acid, for their antibacterial potency. This research highlighted the impact of the trifluoromethoxy group on the antibacterial activity against organisms like Escherichia coli and Bacillus cereus (Adamczyk-Woźniak et al., 2021) .

Photodecarboxylation Studies

Burns and Lukeman (2010) conducted a study on CF3-substituted phenylacetic and mandelic acids, which are structurally similar to 3-(Trifluoromethoxy)phenylacetic Acid. They demonstrated efficient photodecarboxylation of these compounds, leading to the production of trifluoromethyltoluenes and trifluoromethylbenzyl alcohols. This research contributes to our understanding of the photochemical behavior of trifluoromethyl-substituted compounds (Burns & Lukeman, 2010) .

Peptide Synthesis Applications

The 3-nitro-2-pyridinesulfenyl (Npys) group, as discussed by Matsueda and Walter (2009), is useful in peptide synthesis, showing resistance to trifluoroacetic acid. This research indirectly relates to 3-(Trifluoromethoxy)phenylacetic Acid in the context of resistance to certain acids and applications in peptide synthesis (Matsueda & Walter, 2009).

Recovery and Extraction Studies

Phenylacetic acid, which is structurally related to 3-(Trifluoromethoxy)phenylacetic Acid, has been studied extensively in the context of recovery and extraction processes. Wasewar et al. (2015) explored the reactive extraction of phenylacetic acid, demonstrating its significance in the pharmaceutical industry, especially in the production of antibiotics. This research provides insights into the extraction and recovery mechanisms applicable to similar compounds (Wasewar et al., 2015).

Safety And Hazards

When handling 3-(Trifluoromethoxy)phenylacetic Acid, it is recommended to avoid all personal contact, including inhalation. Protective clothing should be worn when there is a risk of exposure. The compound should be used in a well-ventilated area and contact with moisture should be avoided . If skin or eye irritation occurs, medical advice should be sought .

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