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N-Phenyl-bis(trifluoromethanesulfonimide)

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N-Phenyl-bis(trifluoromethanesulfonimide) Basic information

Product Name:
N-Phenyl-bis(trifluoromethanesulfonimide)
Synonyms:
  • phenyltrifluoromethanesulfonimide
  • N-PHENYLBIS(TRIFLUOROMETHANESULFONIMIDE)
  • N-PHENYLBIS(TRIFLUOROMETHANESULPHONIMIDE)
  • N-PHENYLTRIFLUOROMETHANESULFONIMIDE
  • N-PHENYLTRIFLUOROMETHANESULPHONIMIDE
  • N,N-BIS(TRIFLUOROMETHYLSULFONYL)ANILINE
  • 1,1,1-TRIFLUORO-N-PHENYL-N-[(TRIFLUOROMETHYL)SULFONYL]METHANESULFONAMIDE
  • N-Phenylbis(trifluoromethanesulphonimide), Phenyl triflimide
CAS:
37595-74-7
MF:
C8H5F6NO4S2
MW:
357.25
EINECS:
609-445-0
Product Categories:
  • API intermediates
  • 37595-74-7
Mol File:
37595-74-7.mol
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N-Phenyl-bis(trifluoromethanesulfonimide) Chemical Properties

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
InChIKey
DIOHEXPTUTVCNX-UHFFFAOYSA-N
SMILES
C(F)(F)(F)S(N(C1=CC=CC=C1)S(C(F)(F)F)(=O)=O)(=O)=O
CAS DataBase Reference
37595-74-7(CAS DataBase Reference)
NIST Chemistry Reference
N-phenyltrifluoromethanesulfonimide(37595-74-7)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
21
TSCA 
No
HazardClass 
IRRITANT
HS Code 
29242100

MSDS

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N-Phenyl-bis(trifluoromethanesulfonimide) Usage And Synthesis

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

Uses

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.

Uses

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).

N-Phenyl-bis(trifluoromethanesulfonimide)Supplier

Time Chemical Co., Ltd. Gold
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