696-02-6 | 1-Chloro-3,4-difluorobenzene

CAS:696-02-6 | 1-Chloro-3,4-difluorobenzene,Description

1-Chloro-3,4-difluorobenzene is a compound with the molecular formula C6H3ClF2. It is also known by other names such as 4-Chloro-1,2-difluorobenzene and 3,4-Difluorochlorobenzene. This compound is used as a chemical intermediate in the preparation of various other compounds.

Synthesis Analysis

The synthesis of 1-Chloro-3,4-difluorobenzene can be achieved by reacting 2,4-difluoroaniline with t-butyl nitrite in the presence of a boron trifluoride etherate complex. The resulting diazonium salts are then thermally decomposed to yield the desired product.

Molecular Structure Analysis

The molecular structure of 1-Chloro-3,4-difluorobenzene consists of a benzene ring with chlorine and fluorine substituents. The InChI representation of the molecule is InChI=1S/C6H3ClF2/c7-4-1-2-5(8)6(9)3-4/h1-3H.

Physical And Chemical Properties Analysis

1-Chloro-3,4-difluorobenzene is a clear, colorless to light yellow liquid. It has a molecular weight of 148.54 g/mol. The compound has a boiling point of 126 °C and a density of 1.33 g/mL at 25 °C. Its refractive index is 1.475.

Scientific Research Applications

Application 1: Synthesis of Fluorinated Halonitrobenzenes and Halonitrophenols

• Scientific Field: Chemical Synthesis
• Summary of the Application: 1-Chloro-3,4-difluorobenzene is used as a starting building block in the synthesis of fluorinated halonitrobenzenes and halonitrophenols.
• Methods of Application or Experimental Procedures: 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 research resulted in the successful synthesis of fluorinated halonitrobenzenes and halonitrophenols.

Application 2: Synthesis of 2,3-Difluorohalobenzenes

• Scientific Field: Chemical Synthesis
• Summary of the Application: 1-Chloro-3,4-difluorobenzene is used in the three-step regioselective synthesis of 2,3-difluorohalobenzenes.
• Methods of Application or Experimental Procedures: The gas-phase copyrolysis of tetrafluoroethylene and buta-1,3-diene in a flow tube reactor at 490–510 °C gives 3,3,4,4-tetrafluorocyclohex-1-ene, which is selectively converted to 1-bromo- or 1-chloro-2,3-difluorobenzene via intermediate steps of halogenation and dehydrohalogenation.
• Results or Outcomes: The research resulted in the successful synthesis of 2,3-difluorohalobenzenes.

Application 3: Preparation of 1-chloro-4,5-difluoro-2-nitrobenzene

• Scientific Field: Chemical Synthesis
• Summary of the Application: 1-Chloro-3,4-difluorobenzene may be used in the preparation of 1-chloro-4,5-difluoro-2-nitrobenzene.
• Results or Outcomes: The research resulted in the successful synthesis of 1-chloro-4,5-difluoro-2-nitrobenzene.

Application 4: Preparation of Difluoroarenes

• Scientific Field: Chemical Synthesis
• Summary of the Application: 1-Chloro-3,4-difluorobenzene is used in the preparation of difluoroarenes.
• Results or Outcomes: The research resulted in the successful synthesis of difluoroarenes.

Application 5: Preparation of 1-chloro-4,5-difluoro-2-nitrobenzene

• Scientific Field: Chemical Synthesis
• Summary of the Application: 1-Chloro-3,4-difluorobenzene may be used in the preparation of 1-chloro-4,5-difluoro-2-nitrobenzene.
• Results or Outcomes: The research resulted in the successful synthesis of 1-chloro-4,5-difluoro-2-nitrobenzene.

Application 6: Preparation of Difluoroarenes

• Scientific Field: Chemical Synthesis
• Summary of the Application: 1-Chloro-3,4-difluorobenzene is used in the preparation of difluoroarenes.
• Results or Outcomes: The research resulted in the successful synthesis of difluoroarenes.

Safety And Hazards

1-Chloro-3,4-difluorobenzene is flammable and may cause harm if swallowed or if it comes into contact with the skin or eyes. It is recommended to handle this compound with care, using appropriate personal protective equipment.

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