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N,N-Bis(trifluoromethylsulfonyl)aniline

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Name

N,N-Bis(trifluoromethylsulfonyl)aniline

EINECS 609-445-0
CAS No. 37595-74-7 Density 1.766 g/cm3
PSA 88.28000 LogP 4.35380
Solubility solubile in methanol Melting Point 100-102 °C
Formula C8H5F6NO4S2 Boiling Point 305.3 °C at 760 mmHg
Molecular Weight 357.254 Flash Point 138.4 °C
Transport Information N/A Appearance white to off-white crystalline powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 37595-74-7 (N-Phenyl-bis(trifluoromethanesulfonimide)) Hazard Symbols IrritantXi
Synonyms

1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide;N-Phenyl-N-[(trifluoromethyl)sulfonyl]trifluoromethanesulfonamide;N-Phenylbis(trifluoromethanesulfonimide);N-Phenyltriflimide;N-Phenyltrifluoromethylsulfonimide;Phenyl triflimide;Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide;N-Phenylbis(trifluoromethanesulphonimide);

Article Data 23

N,N-Bis(trifluoromethylsulfonyl)aniline Synthetic route

358-23-6

trifluoromethylsulfonic anhydride

62-53-3

aniline

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; aniline With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 40℃; under 600.06 - 1725.17 Torr; for 8h; Sealed tube; Large scale;
Stage #2: With dmap In dichloromethane; acetonitrile under 450.045 - 1575.16 Torr; for 15h; Sealed tube; Large scale;
94%
With triethylamine In dichloromethane at 25℃; for 16h; Inert atmosphere; Industry scale; Cooling with ice;86%
With triethylamine In dichloromethane at 20℃; Cooling with ice;86%

C10F17IN2O8S4

82113-65-3

bis(trifluoromethanesulfonyl)amide

71-43-2

benzene

A

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

B

C14H5F11INO4S2

Conditions
ConditionsYield
at 120℃; Glovebox;A 7%Spectr.
B 93%
335-05-7

Trifluoromethanesulfonyl fluoride

62-53-3

aniline

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
Stage #1: Trifluoromethanesulfonyl fluoride; aniline With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; under 675.068 Torr; for 8h; Sealed tube; Large scale;
Stage #2: With dmap In toluene at 60℃; under 750.075 - 1950.2 Torr; for 10h; Pressure; Solvent; Sealed tube; Large scale;
92.1%
With dmap; potassium carbonate In dichloromethane at -40 - 0℃; under 150.015 - 750.075 Torr; for 12h; Reagent/catalyst;90.7%

Li(1+)*C6H5N(SO2CF3)(1-)=C6H5NLi(SO2CF3)

421-83-0

trifluoromethane sulfonyl chloride

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
In tetrahydrofuran60%
In tetrahydrofuran60%

Na(1+)*CF3SO2NC6H5(1-)=NaCF3SO2NC6H5

358-23-6

trifluoromethylsulfonic anhydride

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
In freon 113=1,1,2-trichloro-trifluoroethane at 95°C;34%
In 1,1,2-Trichloro-1,2,2-trifluoroethane
369-57-3

benzenediazonium tetrafluoroborate

174899-83-3

1-butyl-3-methylimidazolium trifluoromethanesulfonimide

A

C8H5F6NO4S2

B

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
With [Bmim][Br] at 24.84℃; for 24h; Kinetics;
at 24.84℃; for 24h; Kinetics;
369-57-3

benzenediazonium tetrafluoroborate

174899-83-3

1-butyl-3-methylimidazolium trifluoromethanesulfonimide

A

C8H5F6NO4S2

B

462-06-6

fluorobenzene

C

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
at 90℃; for 0.216667h;
1025373-45-8

trifluoromethanesulfonic acid anhydride

62-53-3

aniline

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;
421-83-0

trifluoromethane sulfonyl chloride

62-53-3

aniline

37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

38923-57-8

methyl 2,2-dimethyl-3-oxobutanoate

143225-17-6

methyl 2,2-dimethyl-3-0-(trifluoromethanesulfonate)-but-3-enoate

Conditions
ConditionsYield
Stage #1: methyl 2,2-dimethyl-3-oxobutanoate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane at -78℃; for 1.25h; Inert atmosphere;
100%
Stage #1: methyl 2,2-dimethyl-3-oxobutanoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 0.166667h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide at -10℃; for 2h;
87%
With lithium diisopropyl amide In tetrahydrofuran -78 deg C to RT;
Stage #1: methyl 2,2-dimethyl-3-oxobutanoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.258333h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane Inert atmosphere;

N,N-Bis(trifluoromethylsulfonyl)aniline Chemical Properties

Product Name: N-Phenylbis(trifluoromethanesulphonimide) (CAS NO.37595-74-7)

Molecular Formula: C8H5F6NO4S2
Molecular Weight: 357.25g/mol
Mol File: 37595-74-7.mol
Appearance: white to off-white crystalline powder
Melting Point: 100-102 °C
Boiling point: 305.3 °C at 760 mmHg
Flash Point: 138.4 °C
Density: 1.766 g/cm3
Surface Tension: 44.6 dyne/cm
Enthalpy of Vaporization: 54.57 kJ/mol
Vapour Pressure: .000828 mmHg at 25°C
XLogP3-AA: 3.1
H-Bond Donor: 0
H-Bond Acceptor: 11
Structure Descriptors of N-Phenylbis(trifluoromethanesulphonimide) (CAS NO.37595-74-7):
  IUPAC Name: 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide
  Canonical SMILES: C1=CC=C(C=C1)N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F
  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
Product Categories: API intermediates 

N,N-Bis(trifluoromethylsulfonyl)aniline Safety Profile

Safety Information of N-Phenylbis(trifluoromethanesulphonimide) (CAS NO.37595-74-7):
Hazard Codes: XiIrritant
Risk Statements: 36/37/38  
R36/37/38:Irritating to eyes, respiratory system and skin. 
Safety Statements: 26-36 
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
HazardClass: IRRITANT

N,N-Bis(trifluoromethylsulfonyl)aniline Specification

 N-Phenylbis(trifluoromethanesulphonimide) , its CAS NO. is 37595-74-7, the synonyms are 1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide ; N,N-Bis(trifluoromethylsulfonyl)aniline . 

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