653-22-5

Basic information

• Product Name: N-(pentafluorophenyl)acetamide
• CAS NO: 653-22-5
• Molecular Formula: C₈H₄F₅NO
• Molecular Weight: 225.1155
• Mol File: 653-22-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 229.1°C at 760 mmHg
• Flash Point: 92.3°C
• Density: 1.568g/cm³
• Vapor Pressure: 0.0709mmHg at 25°C
• Refractive Index: 1.476
• CAS DataBase Reference: N-(pentafluorophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(pentafluorophenyl)acetamide(653-22-5)
• EPA Substance Registry System: N-(pentafluorophenyl)acetamide(653-22-5)

Safety Data

• Hazardous Substances Data: 653-22-5(Hazardous Substances Data)

Upstream product

• 60-35-5 acetamide 
• 392-56-3 Hexafluorobenzene 
• 31469-89-3 4-azido-2,3,5,6-tetrafluorobenzonitrile 
• 507-09-5 tiolacetic acid 
• 64317-34-6 N-(pentafluorophenyl)carbonimidoyl dichloride 
• 64-19-7 acetic acid 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 108-24-7 acetic anhydride 

Downstream Products

• 366-50-7 N-(2,4,5-trifluorophenyl)acetamide 
• 365-18-4 2,3,5-trifluoroacetanilide 

Relevant articles and documents

A Selective Single Step Amidation of Polyfluoroarenes

This chemistry establishes a method for the synthesis of per- and poly-fluoroaryl acid amides, utilizing nucleophilic aromatic substitution. Traditionally, such amides are constructed in a two-step process, namely, ammonolysis and then N-acylation. Herein, good yields of N-polyfluoroaryl acid amides were achieved in a single step under mild reaction conditions. Key to achieving optimal yields is the use of two equivalents of the nucleophile. In addition, the mechanism of the reaction is discussed which has implications for other related nucleophilic substitutions.

Conformational analysis of N-aryl-N-(2-azulenyl)acetamides

Aromatic amides bearing 2-azulenyl group on the amide nitrogen were synthesized and their structures were investigated. The π-electron density of the N-aryl group was found to influence the cis-trans conformational preferences of these compounds in solution. X-ray crystallography revealed that the plane of the 2-azulenyl ring has a strong tendency to lie coplanar with the amide plane when the azulene group is located on the same side as the amide oxygen atom.

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.