395-03-9

Basic information

• Product Name: methyl-phenyl-carbamoyl fluoride
• CAS NO: 395-03-9
• Molecular Weight: 153.156
• Mol File: 395-03-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl-phenyl-carbamoyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: methyl-phenyl-carbamoyl fluoride(395-03-9)
• EPA Substance Registry System: methyl-phenyl-carbamoyl fluoride(395-03-9)

Safety Data

• Hazardous Substances Data: 395-03-9(Hazardous Substances Data)

Upstream product

• 353-50-4 Carbonyl fluoride 
• 100-61-8 N-methylaniline 
• 353-49-1 fluoroformyl chloride 
• 124-38-9 carbon dioxide 

Relevant articles and documents

Direct Synthesis of Carbamoyl Fluorides by CO2 Deoxyfluorination

Herein, a new concept for the direct synthesis of carbamoyl fluoride derivatives is disclosed. The developed method makes use of CO2 as an inexpensive and abundant C1 source; a variety of amines were successfully converted in the presence of a deoxyfluorinating reagent. The corresponding products were often obtained in excellent yields under mild reaction conditions (1 atm and room temperature). The reaction was easily scaled up, demonstrating the efficiency of the developed process.

N-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist's Toolbox

Introducing trifluoromethyl groups is a common strategy to improve the properties of biologically active compounds. However, N-Trifluoromethyl moieties on amines and azoles are very rarely used. To evaluate their suitability in drug design, we synthesized a series of N-Trifluoromethyl amines and azoles, determined their stability in aqueous media, and investigated their properties. We show that N-Trifluoromethyl amines are prone to hydrolysis, whereas N-Trifluoromethyl azoles have excellent aqueous stability. Compared to their N-methyl analogues, N-Trifluoromethyl azoles have a higher lipophilicity and can show increased metabolic stability and Caco-2 permeability. Furthermore, N-Trifluoromethyl azoles can serve as bioisosteres of N-iso-propyl and N-Tert-butyl azoles. Consequently, we suggest that N-Trifluoromethyl azoles are valuable substructures to be considered in medicinal chemistry.