ChemicalBook--->CAS DataBase List--->37595-74-7

37595-74-7

37595-74-7 Structure

37595-74-7 Structure
IdentificationMore
[Name]

N,N-Bis(trifluoromethylsulfonyl)aniline
[CAS]

37595-74-7
[Synonyms]

1,1,1-TRIFLUORO-N-PHENYL-N-[(TRIFLUOROMETHYL)SULFONYL]METHANESULFONAMIDE
N,N-BIS(TRIFLUOROMETHYLSULFONYL)ANILINE
N-PHENYLBIS(TRIFLUOROMETHANESULFONIMIDE)
N-PHENYLBIS(TRIFLUOROMETHANESULPHONIMIDE)
N-PHENYLTRIFLUOROMETHANESULFONIMIDE
N-PHENYLTRIFLUOROMETHANESULPHONIMIDE
PHENYL TRIFLIMIDE
phenyltrifluoromethanesulfonimide
N,N-Bis(trifluoromethanesulphonyl)aniline~Phenyl triflimide~N-Phenyltrifluoromethanesulphonimide
Phenyl triflimide~N-Phenyltrifluoromethanesulphonimide
N-PHENYL-BIS-(TRIFLUORMETHANSULFONIMID)
N,N-BIS-(TRIFLUOROMETHANESULFONYL)ANILINE
1,1,1-Trifluoro-N-phenyl-N-(trifluoromethyl)sulphonylmethanesulphonamide
N-Phenylbis(trifluoromethanesulphonimide)97%
n-phenylbis(trifluorometanesulfonimide)
N-Phenyl-bis(trifluoromethyl)sulfonimide
N-Phenylbis(trifluoromethanesulfonimide) [Triflating Reagent]
N-phenyl-bis(trifluoromethanesulfonamide)
N,N-Bis(trifluoromethylsulfonyl)aniline, N-Phenyl-trifluoromethanesulfonimide, Phenyl triflimide, 1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
N-Phenylbis(trifluoromethanesulfonyl)amine
[EINECS(EC#)]

609-445-0
[Molecular Formula]

C8H5F6NO4S2
[MDL Number]

MFCD00000404
[Molecular Weight]

357.25
[MOL File]

37595-74-7.mol
Chemical PropertiesBack Directory
[Appearance]

white to off-white crystalline powder
[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)
[Storage Precautions]

Moisture sensitive
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[F ]

21
[Hazard Note ]

Irritant
[TSCA ]

No
[REACH Registrations]

Active
[HazardClass ]

IRRITANT
[HS Code ]

29350090
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Sodium hydroxide-->Tetrahydrofuran-->Dichloromethane-->Potassium carbonate-->Magnesium sulfate-->Triethylamine-->Sodium chloride-->Sodium hydride-->Aniline-->Trifluoromethanesulfonic anhydride-->Trifluoromethanesulfonyl chloride
[Preparation Products]

1-Boc-4-methanesulfonyloxypiperidine-->2-(triMethylsilyl)ethyl 4-(trifluoroMethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate-->1-Cyclohexen-1-yl trifluoromethane--->Methyl 3-((Trifluoromethylsulfonyl)oxy)phenylacetate
Hazard InformationBack Directory
[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 usefu l in pharmaceutical application.
[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).
[References]

[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
Spectrum DetailBack Directory
[Spectrum Detail]

N-Phenyl-bis(trifluoromethanesulfonimide)(37595-74-7)1HNMR
N-Phenyl-bis(trifluoromethanesulfonimide)(37595-74-7)FT-IR
N-Phenyl-bis(trifluoromethanesulfonimide)(37595-74-7)Raman
N-Phenyl-bis(trifluoromethanesulfonimide)(37595-74-7)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

N-Phenylbis(trifluoromethanesulfonimide), 97%(37595-74-7)
[Alfa Aesar]

N-Phenylbis(trifluoromethanesulfonimide), 99%(37595-74-7)
[Sigma Aldrich]

37595-74-7(sigmaaldrich)
[TCI AMERICA]

N-Phenylbis(trifluoromethanesulfonimide)  [Triflating Reagent],>98.0%(GC)(37595-74-7)
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