169468-83-1 | 2-Chloro-3,4-difluoronitrobenzene

CAS:169468-83-1 | 2-Chloro-3,4-difluoronitrobenzene,Description

Synthesis Analysis

The synthesis of halogenated nitrobenzenes typically involves the introduction of nitro and halogen groups into the benzene ring. For example, the synthesis of 2,4-dichlorofluorobenzene involves diazotization of 2,4-dichloroaniline followed by substitution with fluorine. Similarly, 2,3,4-Trifluoronitrobenzene is synthesized from 2,6-dichlorofluorobenzene through nitration and subsequent fluorination. These methods could potentially be adapted for the synthesis of 2-Chloro-3,4-difluoronitrobenzene by choosing appropriate starting materials and reagents.

Molecular Structure Analysis

The molecular structure of halogenated nitrobenzenes is characterized by the presence of electron-withdrawing nitro and halogen groups attached to the benzene ring. These substituents influence the electronic properties of the molecule and can activate or deactivate the ring towards further chemical reactions. The crystal structure of 1,3,5-trichloro-2,4,6-trifluorobenzene has been determined using X-ray and neutron diffraction, revealing a planar molecule with significant internal vibrations. This information is valuable for understanding the molecular geometry and electronic distribution in similar compounds like 2-Chloro-3,4-difluoronitrobenzene.

Chemical Reactions Analysis

The presence of nitro and halogen groups in halogenated nitrobenzenes makes them susceptible to nucleophilic substitution reactions. For instance, the introduction of fluorine-containing substituents into the aromatic ring enhances the activation of the halogen substituent towards nucleophilic attack, as seen in the synthesis of various derivatives from 1-chloro-2-nitrobenzene and 1-chloro-2,6-dinitrobenzene. These reactions allow for the introduction of various functional groups into the benzene ring, which could be applicable to 2-Chloro-3,4-difluoronitrobenzene for further functionalization.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated nitrobenzenes are influenced by their molecular structure. The introduction of electron-withdrawing groups such as nitro and halogen atoms can increase the compound's reactivity and affect its boiling point, melting point, and solubility. For example, the solvate structure of 1-chloro-3,4-dinitrobenzene with 1,4-dioxane forms a continuous two-dimensional sheet through hydrogen bonding. These properties are crucial for the practical applications of these compounds in chemical synthesis and industry. The specific properties of 2-Chloro-3,4-difluoronitrobenzene would need to be determined experimentally, but they are likely to be similar to those of related compounds.

Scientific Research Applications

Synthesis of Fluorinated Halonitrobenzenes

• Scientific Field: Organic Chemistry
• Application Summary: 2-Chloro-3,4-difluoronitrobenzene is used in the synthesis of fluorinated halonitrobenzenes and halonitrophenols.
• Method of Application: The gas-phase copyrolysis of tetrafluoroethylene with buta-1,3-diene in a flow reactor at 495–505 °C produces 3,3,4,4-tetrafluorocyclohex-1-ene, which selectively converted to 1,2-difluorobenzene or 1-chloro-2,3-difluorobenzene. The latter can be converted to 2-chloro-3,4-difluoronitrobenzene, 2,3,4-trifluoronitrobenzene, 2,3-difluoro-6-nitrophenol, or 2-chloro-3-fluoro-4-nitrophenol via nitration, fluorodechlorination, and hydrolysis reactions.
• Results or Outcomes: The synthesis process results in various fluorinated halonitrobenzenes and halonitrophenols.

Nitration Reaction in Continuous-Flow Microreactor

• Scientific Field: Chemical Engineering
• Application Summary: Although not directly related to 2-Chloro-3,4-difluoronitrobenzene, a similar compound, 2,4-Difluoronitrobenzene, has been used in a study to investigate the homogeneous nitration reaction process in capillary T-microreactors.
• Method of Application: The study demonstrated that the homogeneous nitration reaction process in capillary T-microreactors is greatly influenced by the limitations of mixing. To improve the mixing effectiveness, the researchers investigated the intensification of liquid mixing in the heart mixer plate reactor.
• Results or Outcomes: Compared with the capillary T-microreactor, the mixing effectiveness in the heart mixer plate reactor is improved by three orders of magnitude, resulting in a conversion rate of 98.5% and a reduction in residence time by two orders of magnitude compared to batch reactors.

Preparation of Anti-inflammatory Compound

• Scientific Field: Medicinal Chemistry
• Application Summary: A similar compound, 2,4-difluoroaniline, which can be obtained by reducing a nitro compound, is used as an intermediate for the preparation of the anti-inflammatory compound 2’,4’-difluoro-4-hydroxy (1,1’-biphenyl)-3-carboxylic acid.
• Method of Application: The nitro compound is reduced to give 2,4-difluoroaniline. This is then used in the synthesis of the anti-inflammatory compound.
• Results or Outcomes: The anti-inflammatory compound 2’,4’-difluoro-4-hydroxy (1,1’-biphenyl)-3-carboxylic acid is produced, which is sold under the trade name "DIFLUNISAL".

Preparation of Xanthones and Acridones

• Scientific Field: Organic Chemistry
• Application Summary: 3,4-Difluoronitrobenzene, a compound similar to 2-Chloro-3,4-difluoronitrobenzene, has been used in the preparation of xanthones and acridones.
• Method of Application: The specific methods of application or experimental procedures were not detailed in the source.
• Results or Outcomes: The synthesis process results in the production of xanthones and acridones.

Synthesis of 2,4-Difluoro-5-Nitrobenzenesulfonic Acid

• Scientific Field: Organic Chemistry
• Application Summary: 2,4-Difluoronitrobenzene, another similar compound, has been used in the synthesis of 2,4-difluoro-5-nitrobenzenesulfonic acid via a sulfonation reaction.
• Method of Application: The compound 2,4-difluoronitrobenzene undergoes a sulfonation reaction to produce 2,4-difluoro-5-nitrobenzenesulfonic acid.
• Results or Outcomes: The synthesis process results in the production of 2,4-difluoro-5-nitrobenzenesulfonic acid.

Synthesis of Fluorine Compounds

• Scientific Field: Organic Chemistry
• Application Summary: 2-Chloro-3,4-difluoronitrobenzene is used in the synthesis of various fluorine compounds.
• Method of Application: The gas-phase copyrolysis of tetrafluoroethylene with buta-1,3-diene in a flow reactor at 495–505 °C produces 3,3,4,4-tetrafluorocyclohex-1-ene, which selectively converted to 1,2-difluorobenzene or 1-chloro-2,3-difluorobenzene. The latter can be converted to 2-chloro-3,4-difluoronitrobenzene, 2,3,4-trifluoronitrobenzene, 2,3-difluoro-6-nitrophenol, or 2-chloro-3-fluoro-4-nitrophenol via nitration, fluorodechlorination, and hydrolysis reactions.
• Results or Outcomes: The synthesis process results in various fluorine compounds.

Preparation of Fluoroaniline

• Scientific Field: Medicinal Chemistry
• Application Summary: A similar compound, 2,4-difluoroaniline, which can be obtained by reducing a nitro compound, is used as an intermediate for the preparation of the anti-inflammatory compound 2’,4’-difluoro-4-hydroxy (1,1’-biphenyl)-3-carboxylic acid.
• Method of Application: The nitro compound is reduced to give 2,4-difluoroaniline. This is then used in the synthesis of the anti-inflammatory compound.
• Results or Outcomes: The anti-inflammatory compound 2’,4’-difluoro-4-hydroxy (1,1’-biphenyl)-3-carboxylic acid is produced, which is sold under the trade name "DIFLUNISAL".

Safety And Hazards

The safety data sheet for 2-Chloro-3,4-difluoronitrobenzene indicates that it may cause skin and eye irritation, and may also cause respiratory irritation. It is recommended to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes.

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