653-27-0

Usage

Uses

Used in Organic Synthesis:
Acetamide, 2,2,2-trifluoro-N-(pentafluorophenyl)is used as a reagent in organic synthesis for its unique structure and properties. The presence of fluorinated groups allows for specific interactions with other molecules, facilitating the formation of desired compounds in chemical reactions.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Acetamide, 2,2,2-trifluoro-N-(pentafluorophenyl)is employed as a valuable tool in drug discovery and development. Its stability and ability to interact with biological targets make it an ideal candidate for the design and synthesis of new drugs, potentially leading to the creation of more effective treatments for various diseases and conditions.
Used in Chemical Research:
Acetamide, 2,2,2-trifluoro-N-(pentafluorophenyl)is also utilized in chemical research to study the effects of fluorination on the properties and reactivity of compounds. Its unique structure provides insights into the behavior of fluorinated molecules, which can be applied to the development of new materials and technologies.

Upstream product

• 853-75-8 N-pentafluorophenyl-pentafluorophenylaldimine 
• 407-25-0 trifluoroacetic anhydride 
• 97580-75-1 bis(α-pentafluoroanilino-2,3,4,5,6-pentafluorobenzyl)peroxide 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 55759-55-2 1,1,1-trifluoro-3-(triphenylphosphoranylidene)-2-propanone 

Relevant academic research and scientific papers

α,α,α,2,3,4,5,6-Octafluoroacetanilide

Acetanilide and its derivatives have been the subject of some interest because of certain anomalous properties of the vibrational spectrum of the amide group. In the title compound, C8HF8NO, the molecules are linked through N-H···O hydrogen bonds, with an intermolecular N···O distance of 2.894 (9) angstroms. They form chains parallel to the b axis which are stacked one on top of another in the c direction.

Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control

The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H's. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.