N-Phenyl-bis(trifluoromethanesulfonimide)

N-Phenylbis(trifluoromethanesulfonimide) acts as a mild triflating reagent as well as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes. It is also employed as a reactant for the preparation of amphoteric alfa-boryl aldehydes. It plays an important role in the enantioselective synthesis of the core ring skeleton of leucosceptroids A-D and in steroselective sulfoxidation. 

white to off-white crystalline powder

Acts as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes

Reactant for:
Synthesis of amphoteric alpha-boryl aldehydes
Enantioselective synthesis of core ring skeleton of leucosceptroids A-D
Stereoselective synthesis of monoamine reuptake inhibitor NS9544 acetate
Stereoselective sulfoxidation

N-Phenylbis(trifluoromethanesulfonamide) is used in the enantioselective synthesis of β-amino acids via the Mannich reaction. Used in the synthesis of sphingosine 1-phosphate-1 receptor agonists useful in pharmaceutical application.

Add methylene chloride, aniline, 4-dimethylaminopyridine (DMAP), and triethylamine to a reactor equipped with a thermometer, distillation device, and mechanical stirring. When the vacuum of the reactor is evacuated to -0.095MPa and cooled to -40°C, trifluoromethanesulfonyl fluoride gas is introduced and then stirred at -20°C ~ 0°C and 0.02MPa ~ 0.1MPa reaction pressure, and react for 6 hours Finally, the excess trifluoromethanesulfonyl fluoride gas in the reactor is released and collected by cooling. After the inside of the reactor is brought to normal pressure, 500 mL of water is added, and the liquid is separated. A light yellow solid is obtained after the organic phase is heated to 40°C and methylene chloride is distilled. The light yellow solid is recrystallized with toluene to obtain 650g of white crystal N-Phenyl-bis(trifluoromethanesulfonimide).

[1] Patent: US2012/316204, 2012, A1. Location in patent: Page/Page column 7-8
[2] Patent: WO2015/23967, 2015, A2. Location in patent: Paragraph 0163; 0171
[3] Patent: WO2016/27284, 2016, A2. Location in patent: Page/Page column 69-70
[4] Tetrahedron Letters, 1973, # 46, p. 4607 - 4610
[5] Patent: WO2015/112441, 2015, A1. Location in patent: Page/Page column 58