121602-93-5 | 3,4,5-Trifluorobenzoic acid

CAS:121602-93-5 | 3,4,5-Trifluorobenzoic acid,Description

3,4,5-Trifluorobenzoic acid is a derivative of benzoic acid with three fluorine substituents at para and meta positions. It is part of a group of compounds that have potential inhibitory activity towards d-amino acid oxidases, making them capable of treating mental disorders such as schizophrenia.

Synthesis Analysis

The synthesis of 3,4,5-Trifluorobenzoic acid involves complex chemical reactions. The structure of 3,4,5-trifluorobenzoic acid was analyzed using the Gaussian 16 program.

Molecular Structure Analysis

The molecular formula of 3,4,5-Trifluorobenzoic acid is C7H3F3O2. It has an average mass of 176.093 Da and a monoisotopic mass of 176.008514 Da.

Chemical Reactions Analysis

3,4,5-Trifluorobenzoic acid assists the concerted metalation deprotonation as the C-H activation step, thus facilitating the catalytic cycle. It is also used as a synthetic building block for dibenzoate esters type anticancer drugs.

Physical And Chemical Properties Analysis

3,4,5-Trifluorobenzoic acid has a density of 1.5±0.1 g/cm3. Its boiling point is 251.4±35.0 °C at 760 mmHg. The melting point is 97-99 °C (lit.).

Scientific Research Applications

Synthesis and Chemical Engineering

3,4,5-Trifluorobenzoic acid serves as a valuable synthetic intermediate, especially in the pharmaceutical industry and material science. A study by Deng et al. (2015) demonstrates a continuous microflow process for synthesizing 2,4,5-trifluorobenzoic acid, which is structurally similar and has similar applications. This process involved the generation of an aryl-Grignard reagent and its reaction with gaseous CO2, highlighting the chemical's role in facilitating efficient synthesis techniques (Deng et al., 2015).

Vibrational Spectroscopy and Structural Analysis

3,4,5-Trifluorobenzoic acid is also significant in vibrational spectroscopy. Mukherjee et al. (2010) conducted a detailed study of its Raman and FTIR spectra. They employed DFT and SQM force fields for vibrational analysis in both dimeric and monomeric forms, which assists in understanding the molecular structure and behavior of such compounds (Mukherjee et al., 2010).

Photoelectrochemical Applications

Lima et al. (2022) explored a photoelectrochemical method for amperometric determination of 3,4,5-trihydroxybenzoic acid, another compound structurally related to 3,4,5-trifluorobenzoic acid. This study underscores the potential of such compounds in developing sensitive analytical methods for various samples, including wines and teas (Lima et al., 2022).

Catalysis and Chemical Reactions

The compound plays a role in catalysis as well. Sridhar and Perumal (2005) utilized 3,4,5-trifluorobenzeneboronic acid, closely related to 3,4,5-trifluorobenzoic acid, as a catalyst for the synthesis of 1,4-dihydropyridines, indicating its potential in facilitating various organic reactions (Sridhar & Perumal, 2005).

Material Synthesis

In the field of material synthesis, Hardcastle et al. (2001) described the efficient synthesis of a small library of 4-alkoxy-2-hydroxy-3,5,6-trifluorobenzoic acids. This showcases the use of 3,4,5-trifluorobenzoic acid derivatives in the preparation of diverse chemical libraries, essential for material science research (Hardcastle et al., 2001).

Coordination Chemistry

Sharutin et al. (2004) synthesized compounds using 3,4,5-trifluorobenzoic acid, demonstrating its role in coordination chemistry and the synthesis of complex molecules. This research provides insight into the structural and bonding characteristics of such compounds (Sharutin et al., 2004).

Safety And Hazards

The safety information for 3,4,5-Trifluorobenzoic acid includes hazard statements H315, H319, and H335. It is classified as Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3. Personal protective equipment such as dust mask type N95 (US), eyeshields, and gloves are recommended.

Future Directions

3,4,5-Trifluorobenzoic acid finds its application as a transient directing group in transition metal catalysed C-H activation reactions. A salt of 3,4,5-trifluorobenzoic acid improves the solubility and permeability of naftopidil in benign prostatic hyperplasia treatment. It is also used as a synthetic building block for dibenzoate esters type anticancer drugs.

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