289039-49-2 | 4,5-DICHLORO-2-FLUOROBENZOIC ACID

CAS:289039-49-2 | 4,5-DICHLORO-2-FLUOROBENZOIC ACID,Description

4,5-Dichloro-2-fluorobenzoic acid is a halogenated benzoic acid derivative. While the specific compound is not directly discussed in the provided papers, related compounds with similar substitution patterns on the benzene ring are mentioned. These compounds are often used as building blocks in organic synthesis, particularly in the creation of heterocyclic compounds which are of significant importance in drug discovery.

Synthesis Analysis

The synthesis of halogenated benzoic acid derivatives typically involves multistep reactions. For instance, 4-chloro-2-fluoro-5-nitrobenzoic acid, a compound with a similar substitution pattern, is synthesized starting from commercially available materials and involves steps such as immobilization on Rink resin, chlorine substitution, and nitro group reduction. Another related compound, 4-chloro-2,5-difluorobenzoic acid, is synthesized from 2,5-difluoroaniline using the Sandmeyer reaction, followed by bromination and a Grignard reaction, with the final product achieving a purity of 99.16% as confirmed by HPLC.

Molecular Structure Analysis

The molecular structure of halogenated benzoic acids is characterized by the presence of halogen atoms attached to the benzene ring, which can significantly influence the physical and chemical properties of the compound. For example, the crystal structure of a related compound, a fumaric acid salt of a chloro-fluorobenzoyl derivative, was determined by X-ray crystallography, indicating that the solid and solution conformations are similar.

Chemical Reactions Analysis

Halogenated benzoic acids can participate in various chemical reactions due to the presence of reactive halogen atoms and the carboxylic acid group. They can act as intermediates in the synthesis of heterocyclic compounds, as seen with 4-chloro-2-fluoro-5-nitrobenzoic acid, which is used to prepare benzimidazoles, benzotriazoles, and other nitrogenous heterocycles. Additionally, these compounds can be used in the detection of other substances, such as the use of a dibenzoic acid derivative for the fluorescent quenching detection of trinitrophenol (TNP) and acetate ions.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzoic acids are influenced by the halogen substituents. These properties include thermal stability, phase transitions, and polymorphism, which can be studied using techniques like thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC). For instance, the fumaric acid salt of a chloro-fluorobenzoyl derivative exhibits a melting point of 157 degrees Celsius. The presence of halogens also affects the acidity of the carboxylic acid group, potentially altering solubility and reactivity.

Scientific Research Applications

• Synthesis of Other Chemical Compounds

  • Field : Organic Chemistry
  • Application : 4,5-Dichloro-2-fluorobenzoic acid is used as a precursor in the synthesis of other chemical compounds.
  • Method : It can be synthesized from the commercially available 4-chloro-3,5-difluorobenzonitrile through a reaction sequence involving nitration, selective reduction, diazotisation, and chlorination.
  • Results : The synthesis of 2,4-dichloro-3,5-difluorobenzoic acid from 4-chloro-3,5-difluorobenzonitrile was achieved in good yield.

• Precursor of Agrochemical and Pharmaceutical Products

  • Field : Agrochemistry and Pharmacology
  • Application : Fluoro- and chloro-substituted benzoic acid derivatives, like 4,5-Dichloro-2-fluorobenzoic acid, are valuable intermediates for the synthesis of agrochemical and pharmaceutical products.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The outcomes of these applications were not specified in the source.
• Intermediate in Medicinal Compounds and Pesticides
  • Field : Medicinal Chemistry and Agrochemistry
  • Application : 4,5-Dichloro-2-fluorobenzoic acid is an important intermediate in the synthesis of medicinal compounds and pesticides.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The outcomes of these applications were not specified in the source.

• Intermediate in the Synthesis of Biologically Active Compounds

  • Field : Biochemistry
  • Application : 4,5-Dichloro-2-fluorobenzoic acid is used as an intermediate in the synthesis of biologically active compounds.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The outcomes of these applications were not specified in the source.

• Intermediate in the Synthesis of Functional Materials

  • Field : Material Science
  • Application : Fluoroarenes, like 4,5-Dichloro-2-fluorobenzoic acid, are versatile components of many synthetic functional materials.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The outcomes of these applications were not specified in the source.

Safety And Hazards

4,5-Dichloro-2-fluorobenzoic acid is classified as a hazardous substance. It may cause respiratory irritation, skin irritation, and serious eye irritation. Precautionary measures include avoiding contact with skin and eyes, not breathing dust, and not ingesting the substance.

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