202664-53-7 | 2'-FLUORO-5'-(TRIFLUOROMETHYL)ACETOPHENONE

CAS:202664-53-7 | 2'-FLUORO-5'-(TRIFLUOROMETHYL)ACETOPHENONE,Description

Conformational Preference Analysis

The study of 2'-fluoro-substituted acetophenone derivatives, including 2'-Fluoro-5'-(trifluoromethyl)acetophenone, has shown that these compounds preferentially adopt an s-trans conformation in solution. This conformational preference is evidenced by through-space spin-spin couplings (TS-couplings) observed in NMR spectra, which are indicative of the spatial proximity of hydrogen and fluorine atoms within the molecule. The consistency of this preference across different solvents, as indicated by the linear correlation of coupling constants with solvent dielectric constants, and the confirmation by X-ray crystallography, suggest that the s-trans conformation is energetically favored, likely due to the repulsion between the polar fluorine and oxygen atoms in the s-cis conformation. These findings have potential implications for drug design, where the conformational stability of a molecule can significantly affect its biological activity.

Synthesis Analysis

The synthesis of ring-fluorinated hetero- and carbocycles from 1,1-difluoro-1-alkenes demonstrates the remarkable effect of vinylic fluorines on facilitating otherwise disfavored 5-endo-trig cyclizations. The presence of fluorine atoms is critical in these reactions, as they enable the intramolecular nucleophilic substitution with the loss of vinylic fluorine, leading to high yields of fluorinated indoles, furans, thiophenes, and cyclopentenes. This synthesis approach highlights the unique reactivity of fluorine-containing compounds and their utility in constructing complex fluorinated structures.

Molecular Structure Analysis

The molecular structure of related fluorophenol compounds has been elucidated using gas-phase electron diffraction. These studies reveal the potential for weak intramolecular hydrogen bonding between hydroxyl and fluorine substituents in ortho positions. Although the strength of these hydrogen bonds is not as strong as in some other fluorinated compounds, their presence can influence the molecular geometry and potentially the reactivity of the molecule. This information is relevant to understanding the behavior of 2'-Fluoro-5'-(trifluoromethyl)acetophenone, as similar intramolecular interactions may be present.

Chemical Reactions Analysis

The synthesis of fluorine-18 labeled compounds, such as fluoronicotinic acid-2,3,5,6-tetrafluorophenyl ester, demonstrates the feasibility of conducting fluorination reactions at room temperature without the need for azeotropic drying of the fluoride. This method, which involves flowing a solution through an anion exchange cartridge, represents a significant simplification and time-saving over traditional methods. Such advancements in fluorination chemistry are crucial for the efficient production of fluorinated molecules, including 2'-Fluoro-5'-(trifluoromethyl)acetophenone, which are increasingly important in pharmaceuticals and materials science.

Physical and Chemical Properties Analysis

The interaction of o-(carboxamido)trifluoroacetophenones with carboxylate anions results in a significant fluorescence "turn-on" effect. This phenomenon is attributed to the stabilization of the anion-ionophore adduct through intramolecular hydrogen bonding, which prevents a possible quenching transition. The large fluorescence enhancement observed with these compounds underscores the importance of understanding the physical and chemical properties of fluorinated acetophenones, as they can have practical applications in sensing technologies.

Scientific Research Applications

Application 1: Agrochemical and Pharmaceutical Industries

• Summary of the Application: 2’-Fluoro-5’-(trifluoromethyl)acetophenone is used in the synthesis of trifluoromethylpyridines, which are key structural motifs in active agrochemical and pharmaceutical ingredients. The major use of these derivatives is in the protection of crops from pests.
• Results or Outcomes: The biological activities of trifluoromethylpyridine derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety. Several trifluoromethylpyridine derivatives are also used in the pharmaceutical and veterinary industries; five pharmaceutical and two veterinary products containing the trifluoromethylpyridine moiety have been granted market approval, and many candidates are currently undergoing clinical trials.

Application 2: Synthesis of Trifluoromethylpyridines

• Summary of the Application: 2’-Fluoro-5’-(trifluoromethyl)acetophenone is used in the synthesis of trifluoromethylpyridines. These compounds are key structural motifs in active agrochemical and pharmaceutical ingredients.
• Results or Outcomes: The biological activities of trifluoromethylpyridine derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety. Several trifluoromethylpyridine derivatives are also used in the pharmaceutical and veterinary industries.

Application 3: Direct Substitution of Chlorine by CF3

• Summary of the Application: 2’-Fluoro-5’-(trifluoromethyl)acetophenone has been used to investigate the use of in situ generated CuCF3 for the direct substitution of chlorine by CF3 in various aromatic substrates.

Application 4: Synthesis of Ascididemin

• Summary of the Application: 2’-Fluoro-5’-(trifluoromethyl)acetophenone has been used as a starting reagent in the synthesis of ascididemin, a marine alkaloid with significant antitumor and antiviral properties.

Application 5: Direct Substitution of Chlorine by CF3

• Summary of the Application: 2’-Fluoro-5’-(trifluoromethyl)acetophenone has been used to investigate the use of in situ generated CuCF3 for the direct substitution of chlorine by CF3 in various aromatic substrates.

Safety And Hazards

This compound is considered hazardous. It may cause skin irritation, serious eye irritation, 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.

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