1391728-13-4 | 1-Fluoro-3,3-dimethyl-1,2-benziodoxole

CAS:1391728-13-4 | 1-Fluoro-3,3-dimethyl-1,2-benziodoxole,Description

“1-Fluoro-3,3-dimethyl-1,2-benziodoxole” is a hypervalent iodine derivative. It is a crystalline, off-white solidthat can be handled under air for extended periods without noticeable hydrolytic decomposition.

Synthesis Analysis

This compound can be used as an electrophilic fluorinating reagent for α-monofluorination of β-ketoesters in the presence of triethylamine trihydrofluoride. Ethyl 3-oxo-3-phenylpropanoate is added to a solution of 1-fluoro-3,3-dimethyl-1,2-benziodoxole in Et3N･3HF. The flask is then sealed and heated to 40 °C for 24 hours.

Molecular Structure Analysis

The molecular formula of “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” is C9H10FIO. Its molecular weight is 280.08 g/mol.

Chemical Reactions Analysis

In the presence of excess fluoride ions (provided by triethylamine-hydrogen fluoride complexes), “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” can effectively function as an electrophilic fluorination reagent for easily enolizable diketo substrates.

Physical And Chemical Properties Analysis

“1-Fluoro-3,3-dimethyl-1,2-benziodoxole” is a solid at 20 °C. It has a melting point of 86.0 to 90.0 °C. It is soluble in methanol.

Scientific Research Applications

Application 1: Fluorination of Organic Compounds

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” is used as an electrophilic fluorinating reagent for the fluorination of organic compounds. The addition of a fluorine atom increases the lipophilicity of the drugs, making it unique in the field of medicinal chemistry.
• Methods of Application or Experimental Procedures : In the presence of excess fluoride ions (provided by triethylamine-hydrogen fluoride complexes), “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” can effectively function as an electrophilic fluorination reagent for easily enolizable diketo substrates.
• Results or Outcomes : The use of “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” in the fluorination of organic compounds has led to the development of various fluorinated aromatic compounds that have been used as drugs to treat various diseases.

Application 2: Difluorination of Styrenes

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” can engage in silver-catalyzed difluorination of styrenes.
• Methods of Application or Experimental Procedures : In the presence of excess fluoride ions (provided by triethylamine-hydrogen fluoride complexes), “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” can engage in silver-catalyzed difluorination of styrenes.

Application 3: Monofluorination of β-ketoesters

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” is used for the monofluorination of β-ketoesters.
• Methods of Application or Experimental Procedures : Ethyl 3-oxo-3-phenylpropanoate (0.062 mL, 0.357 mmol) is added to a solution of 1-fluoro-3,3-dimethyl-1,2-benziodoxole (0.200 g, 0.715 mmol) in Et3N･3HF (0.71 M solution in dichloromethane, 1.4 mL, 0.96 mmol). The flask is then sealed and heated to 40 °C for 24 hours.

Application 4: Fluorination of Sulfides

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” can be applied to various fluorination reactions of sulfides.

Application 5: Hypervalent Iodine-Mediated Fluorination of Organic Compounds

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” is used in hypervalent iodine-mediated fluorination of organic compounds. This method has received particular attention in organic synthesis mainly due to their mild reaction conditions and environmentally friendly nature of hypervalent iodine reagents.
• Results or Outcomes : The use of “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” in the hypervalent iodine-mediated fluorination of organic compounds has led to the development of various fluorinated organic compounds.

Safety And Hazards

This compound can cause skin irritation and serious eye irritation. Therefore, it is recommended to wear protective gloves, eye protection, and face protection when handling it. If it comes into contact with the skin, wash with plenty of water. If eye irritation persists, get medical advice or attention.

Future Directions

As an air- and moisture-stable electrophilic fluorinating reagent, “1-Fluoro-3,3-dimethyl-1,2-benziodoxole” has potential applications in various chemical reactions. Its use in the monofluorination of β-ketoestersand silver-catalyzed difluorination of styrenessuggests that it could be further explored in the field of synthetic chemistry.

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