135748-35-5 | 4-CHLORO-2,5-DIFLUOROBENZONITRILE

CAS:135748-35-5 | 4-CHLORO-2,5-DIFLUOROBENZONITRILE,Description

4-Chloro-2,5-difluorobenzonitrile is a chemical compound that is closely related to various other halogenated benzonitriles. While the specific compound is not directly mentioned in the provided papers, its structural analogs have been studied extensively. These analogs include compounds with similar halogen substitutions on the benzene ring, which are often used as intermediates in the synthesis of more complex molecules, particularly in the pharmaceutical industry.

Synthesis Analysis

The synthesis of halogenated benzonitriles, such as 4-chloro-2,5-difluorobenzonitrile, can be achieved through various methods. One approach is the Sandmeyer reaction, which is used to synthesize 4-chloro-2,5-difluorobenzoic acid from 2,5-difluoroaniline, followed by bromination and a Grignard reaction. Another method involves step-by-step fluorination from dichlorobenzonitrile, which has been shown to be effective in managing side reactions such as polymerization and darkening. These methods highlight the versatility and reactivity of halogenated benzonitriles in chemical synthesis.

Molecular Structure Analysis

The molecular structure of halogenated benzonitriles can be analyzed using various spectroscopic techniques. For instance, vibrational analysis of 4-chloro-3-nitrobenzonitrile was conducted using experimental FT-IR and Raman spectra, as well as theoretical calculations with different computational methods. This analysis provided detailed information on the geometric parameters and vibrational frequencies, which are essential for understanding the physical properties of these compounds.

Chemical Reactions Analysis

Halogenated benzonitriles participate in a variety of chemical reactions due to their reactive halogen atoms and nitrile group. For example, 4-chloro-2-fluoro-5-nitrobenzoic acid can be used as a multireactive building block for the synthesis of various heterocyclic compounds, including benzimidazoles and quinoxalinones. These reactions are crucial for the development of diverse libraries of compounds with potential pharmaceutical applications.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzonitriles are influenced by their molecular structure. For example, the presence of halogen atoms can affect the compound's melting and boiling points, solubility, and stability. The vibrational analysis mentioned earlier provides insights into the molecular properties that dictate these physical characteristics. Additionally, the synthesis and characterization of related compounds, such as 5-chloro-1-(difluorochloro)-2,3,4,5,6,6-hexafluoro-1,3-cyclohexadiene, involve the study of their elemental composition, mass, infrared, and NMR spectroscopy, which are indicative of their physical and chemical behavior.

Scientific Research Applications

Application 1: Synthesis of 2,4-Dichloro-3,5-Difluorobenzoic Acid

• Scientific Field: Chemical Synthesis
• Summary of the Application: 4-Chloro-2,5-difluorobenzonitrile is used as a precursor in the synthesis of 2,4-dichloro-3,5-difluorobenzoic acid. This compound is a valuable intermediate for the synthesis of medicines, including antibacterials.
• Methods of Application or Experimental Procedures: The synthesis of 2,4-dichloro-3,5-difluorobenzoic acid from 4-chloro-2,5-difluorobenzonitrile involves a sequence of reactions including nitration, selective reduction, diazotisation, and chlorination. The synthesis can be accomplished simultaneously in one step.
• Results or Outcomes: The synthesis process yields 2,4-dichloro-3,5-difluorobenzoic acid in good yield. This compound is a synthetic precursor needed to prepare biologically active compounds.

Application 2: Preparation of Amidino Ureas with Antimalarial Activity

• Scientific Field: Pharmaceutical Synthesis
• Summary of the Application: 4-Chloro-2,5-difluorobenzonitrile is used as a precursor in the synthesis of amidino ureas, which have antimalarial activity. This compound is a valuable intermediate for the synthesis of these biologically active compounds.
• Methods of Application or Experimental Procedures: The synthesis of amidino ureas from 4-Chloro-2,5-difluorobenzonitrile involves a sequence of reactions including the reaction of an R1, R2-benzoyl chloride with an alkanesulphonyltrichlorophosphazene at a temperature of between 150* C. and 190* C. The benzonitrile products are useful as intermediates in the preparation of amidino ureas.
• Results or Outcomes: The synthesis process yields amidino ureas, which have shown antimalarial activity.

Application 3: Preparation of 2,4-Dichloro-5-fluorobenzonitrile

• Scientific Field: Chemical Synthesis
• Summary of the Application: 4-Chloro-2,5-difluorobenzonitrile is used as a precursor in the synthesis of 2,4-dichloro-5-fluorobenzonitrile. This compound is a valuable intermediate for the synthesis of chloro-2-difluoro-4,5-benzoic acid.
• Methods of Application or Experimental Procedures: The synthesis of 2,4-dichloro-5-fluorobenzonitrile from 4-Chloro-2,5-difluorobenzonitrile involves a sequence of reactions. The exact procedures and technical details are not specified in the source.
• Results or Outcomes: The synthesis process yields 2,4-dichloro-5-fluorobenzonitrile, which is used as an intermediate in the preparation of chloro-2-difluoro-4,5-benzoic acid.

Safety And Hazards

4-Chloro-2,5-difluorobenzonitrile is classified as harmful if swallowed, in contact with skin, or if inhaled. It can cause skin irritation and serious eye irritation. Therefore, it is recommended to wear personal protective equipment, avoid dust formation, and use only under a chemical fume hood.

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