1077-01-6 | 3-(Trifluoromethoxy)fluorobenzene

CAS:1077-01-6 | 3-(Trifluoromethoxy)fluorobenzene,Description

3-(Trifluoromethoxy)fluorobenzene is a fluorinated aromatic compound that is part of a broader class of aryl trifluoromethyl ethers. These compounds are characterized by the presence of a trifluoromethoxy group (-OCF3) attached to an aromatic ring, which in this case is also substituted with a fluorine atom. The trifluoromethoxy group is of particular interest due to its ability to influence the physical and chemical properties of the molecule, such as increasing its lipophilicity and stability, making it a valuable moiety in medicinal chemistry and materials science.

Synthesis Analysis

The synthesis of aryl trifluoromethyl ethers, including 3-(Trifluoromethoxy)fluorobenzene, can be achieved through a novel strategy that combines O-carboxydifluoromethylation of phenols followed by decarboxylative fluorination. This method utilizes accessible and inexpensive reagents such as sodium bromodifluoroacetate and SelectFluor II, making it practical for the O-trifluoromethylation of phenols. The synthesis protocol has been demonstrated to be effective by preparing a plant-growth regulator, Flurprimidol, which implies its potential application in the synthesis of 3-(Trifluoromethoxy)fluorobenzene.

Molecular Structure Analysis

The molecular structure of fluorobenzene derivatives, including those with trifluoromethoxy groups, can significantly influence their physical properties. For instance, the presence of fluorine atoms in the benzene group can decrease the temperature range of the nematic phase in liquid crystals. The molecular core structure and the number of fluorine atoms also affect the average intermolecular distance, effective molecular length, and optical anisotropy. These findings suggest that the molecular structure of 3-(Trifluoromethoxy)fluorobenzene would have a distinct impact on its physical properties, potentially affecting its applications in various fields.

Chemical Reactions Analysis

The electrophilic fluorination of fluoroaromatics, including trifluoromethylbenzenes, can be promoted using trifluoromethanesulfonic acid as a novel solvent. This process can lead to the formation of various fluorinated products, including difluorobenzene isomers. Although the specific reactivity of 3-(Trifluoromethoxy)fluorobenzene is not detailed, the general behavior of fluorobenzene compounds under electrophilic fluorination conditions provides insight into the types of chemical reactions that such compounds might undergo.

Physical and Chemical Properties Analysis

The physical properties of nematogenic fluorobenzene derivatives are influenced by their molecular core structure and the number of fluorine atoms present. The density, optical anisotropy, and orientational order parameters are among the properties affected. Electrochemical fluorination of trifluoromethylbenzenes can result in a variety of fluorinated products, indicating that the physical and chemical properties of these compounds can be finely tuned through chemical reactions. The crystal structure of polyfluoro-substituted benzenes, including the presence of C–H⋯F–C hydrogen bonding and F⋯F interactions, further illustrates the complex intermolecular interactions that can influence the properties of these compounds.

Scientific Research Applications

Trifluoromethoxylation Reagents

• Scientific Field : Chemistry
• Methods of Application : Until very recently, several innovative reagents were developed to facilitate the trifluoromethoxylation reaction and make CF3O-containing compounds more accessible.
• Results or Outcomes : This advancement has made CF3O-containing compounds more accessible and has opened up new possibilities for their use in various fields.

Agrochemical and Pharmaceutical Ingredients

• Scientific Field : Agrochemical and Pharmaceutical Industries
• Application Summary : Trifluoromethylpyridines (TFMP), which can be derived from “3-(Trifluoromethoxy)fluorobenzene”, are used as a key structural motif in active agrochemical and pharmaceutical ingredients. Currently, the major use of TFMP derivatives is in the protection of crops from pests.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results or Outcomes : More than 20 new TFMP-containing agrochemicals have acquired ISO common names. Several TFMP derivatives are also used in the pharmaceutical and veterinary industries; five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials.

Safety And Hazards

The safety data sheet for “3-(Trifluoromethoxy)fluorobenzene” indicates that it causes severe skin burns and eye damage, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray and to use only outdoors or in a well-ventilated area.

Future Directions

The trifluoromethoxy functional group has received increasing attention in recent years due to its distinctive properties such as good metabolic stability, appropriate lipophilicity, and special electrical properties. The development of new reagents and new strategies of direct trifluoromethoxylation are attracting the enthusiasm of many fluorine chemical workers.

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