654-87-5 | 2,3,5-TRIFLUOROBENZOIC ACID

CAS:654-87-5 | 2,3,5-TRIFLUOROBENZOIC ACID,Description

2,3,5-Trifluorobenzoic acid is a trifluorinated benzoic acid derivative, which is a compound of interest in various fields such as pharmaceuticals and material science due to its unique chemical properties imparted by the presence of fluorine atoms. Although the provided papers do not directly discuss 2,3,5-trifluorobenzoic acid, they do provide insights into closely related compounds, which can be used to infer some aspects of the synthesis, structure, and reactivity of 2,3,5-trifluorobenzoic acid.

Synthesis Analysis

The synthesis of trifluorobenzoic acid derivatives typically involves halogenated precursors that undergo further chemical transformations. For instance, the synthesis of 2,4,5-trifluorobenzoic acid is reported to be efficiently carried out using a continuous microflow process involving the generation of an aryl-Grignard reagent followed by carboxylation with gaseous CO2. This method could potentially be adapted for the synthesis of 2,3,5-trifluorobenzoic acid by starting with an appropriately substituted bromobenzene.

Molecular Structure Analysis

The molecular structure of trifluorobenzoic acid derivatives is characterized by the presence of a carboxyl group and fluorine atoms attached to a benzene ring. The carboxyl group can exhibit a twist relative to the benzene ring plane, as observed in 3-chloro-2,4,5-trifluorobenzoic acid, where the twist is about 6.8°. This twisting can influence the compound's ability to form hydrogen bonds and, consequently, its physical properties and reactivity.

Chemical Reactions Analysis

Trifluorobenzoic acid derivatives can undergo various chemical reactions, including nitration, reduction, diazotization, and halogenation, as demonstrated in the synthesis of 5-chloro-2,3,4-trifluorobenzoic acid. These reactions are crucial for further functionalizing the benzene ring and for the preparation of more complex molecules, such as pharmaceuticals.

Physical and Chemical Properties Analysis

The physical and chemical properties of trifluorobenzoic acid derivatives are significantly influenced by the electron-withdrawing effect of the fluorine atoms and the carboxyl group. The presence of fluorine atoms increases the acidity of the carboxylic acid group and affects the compound's boiling and melting points. The crystal structure of these compounds often shows typical carboxylic acid dimers linked by hydrogen bonds, which can arrange into sheets or other structures in the solid state. The thermal behavior of related compounds containing trifluorobenzoate ligands has been studied, revealing solvent release as a primary step in thermal decomposition.

Scientific Research Applications

2,3,5-Trifluorobenzoic acid is a chemical compound with the molecular formula C7H3F3O2 and a molecular weight of 176.09. It is a solid powder that is white to light yellow to light orange in color. It has a melting point of 107.0 to 111.0 °C.

While specific applications of 2,3,5-Trifluorobenzoic acid were not found, trifluorobenzoic acids in general have been used in various fields. For example, 2,4,5-Trifluorobenzoic acid is an important intermediate in the synthesis of quinolone antibacterials. Another compound, 3,4,5-Trifluorobenzoic acid, has been used in the synthesis of dibenzoate esters type anticancer drugs.

• 3,4,5-Trifluorobenzoic acid :
  • It is an isomer of 2,3,6-Trifluorobenzoic acid.
  • It has potential inhibitory activity towards d-amino acid oxidases, which could make it capable of treating mental disorders such as schizophrenia.
  • 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.
• 3-Hydroxy-2,4,5-trifluorobenzoic acid :
  • It may be used to synthesize methyl 3-methoxy-2,4,5-trifluorobenzoate and ethyl 3-ethoxy-2,4,5-trifluorobenzoate.
• 3,4,5-Trifluorobenzoic acid :
  • It is an isomer of 2,3,6-Trifluorobenzoic acid.
  • It has potential inhibitory activity towards d-amino acid oxidases, which could make it capable of treating mental disorders such as schizophrenia.
  • 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.
• 3-Hydroxy-2,4,5-trifluorobenzoic acid :
  • It may be used to synthesize methyl 3-methoxy-2,4,5-trifluorobenzoate and ethyl 3-ethoxy-2,4,5-trifluorobenzoate.

Safety And Hazards

2,3,5-Trifluorobenzoic acid is classified as hazardous under the Hazardous Products Regulations. It causes skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray, avoid contacting with skin and eye, use personal protective equipment, wear chemical impermeable gloves, ensure adequate ventilation, remove all sources of ignition, evacuate personnel to safe areas, and keep people away from and upwind of spill/leak.

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