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HomeProduct name listN-Phenyl-bis(trifluoromethanesulfonimide)

N-Phenyl-bis(trifluoromethanesulfonimide)

Synonym(s):N,N-Bis(trifluoromethylsulfonyl)aniline;N-Phenyl-trifluoromethanesulfonimide;1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide;NSC 240874;Phenyl triflimide

  • CAS NO.:37595-74-7
  • Empirical Formula: C8H5F6NO4S2
  • Molecular Weight: 357.25
  • MDL number: MFCD00000404
  • EINECS: 609-445-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-30 18:52:02
N-Phenyl-bis(trifluoromethanesulfonimide) Structural

What is N-Phenyl-bis(trifluoromethanesulfonimide)?

Description

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. 

Chemical properties

white to off-white crystalline powder

The Uses of N-Phenyl-bis(trifluoromethanesulfonimide)

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 usefu l in pharmaceutical application.

The Uses of N-Phenyl-bis(trifluoromethanesulfonimide)

N-Phenyl-bis(trifluoromethanesulfonimide)
To a solution of the SM (798 mg, 3.14 mmol) in DCM (7 mL) was added DMAP (38.3 mg, 0.314 mmol), TEA (1.31 mL, 9.41 mmol), and Tf2NPh (1.68 g, 4.71 mmol). The reaction mixture was stirred at RT for 90 min, after which time it was concentrated in vacuo. The resulting material was purified by Prep LC (50 g silica, 0-20% EtOAc/heptane) to provide the product as a yellow oil which crystallized upon standing. [1.17 g, 97%]

The Uses of N-Phenyl-bis(trifluoromethanesulfonimide)

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.

The Uses of N-Phenyl-bis(trifluoromethanesulfonimide)

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

Synthesis

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).

Properties of N-Phenyl-bis(trifluoromethanesulfonimide)

Melting point: 100-102 °C(lit.)
Boiling point: 305.3±52.0 °C(Predicted)
Density  1.766±0.06 g/cm3(Predicted)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  Soluble in methanol. Slightly soluble in chloroform and ethyl acetate.
form  Crystals or Crystalline Powder
pka -13.12±0.50(Predicted)
color  White or colorless
Sensitive  Moisture Sensitive
BRN  1269141
Stability: Moisture Sensitive
InChI InChI=1S/C8H5F6NO4S2/c9-7(10,11)20(16,17)15(6-4-2-1-3-5-6)21(18,19)8(12,13)14/h1-5H
CAS DataBase Reference 37595-74-7(CAS DataBase Reference)
NIST Chemistry Reference N-phenyltrifluoromethanesulfonimide(37595-74-7)

Safety information for N-Phenyl-bis(trifluoromethanesulfonimide)

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for N-Phenyl-bis(trifluoromethanesulfonimide)

InChIKey DIOHEXPTUTVCNX-UHFFFAOYSA-N
SMILES C(F)(F)(F)S(N(C1=CC=CC=C1)S(C(F)(F)F)(=O)=O)(=O)=O

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