1,1,1-trifluoro-N-phenyl-N-trifluoromethanesulfonylmethanesulfonamide

• ChemBase ID: 12118
• Molecular Formular: C8H5F6NO4S2
• Molecular Mass: 357.2500192
• Monoisotopic Mass: 356.95641897
• SMILES: S(=O)(=O)(N(S(=O)(=O)C(F)(F)F)c1ccccc1)C(F)(F)F
• Canonical SMILES: FC(S(=O)(=O)N(S(=O)(=O)C(F)(F)F)c1ccccc1)(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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1,1-trifluoro-N-phenyl-N-trifluoromethanesulfonylmethanesulfonamide
• IUPAC Traditional name: 1,1,1-trifluoro-N-phenyl-N-trifluoromethanesulfonylmethanesulfonamide
• Synonyms: N-Phenyltrifluoromethanesulfonimide; N-Phenylbis(trifluoromethanesulphonimide), Phenyl triflimide; N,N-Bis(trifluoromethylsulphonyl)aniline 98%; NSC 240874; 1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide; N,N-Bis(trifluoromethylsulfonyl)aniline; N-Phenyl-trifluoromethanesulfonimide; Phenyl triflimide; N-Phenyl-bis(trifluoromethanesulfonimide); N,N-Bis(trifluoromethanesulfonyl)aniline; N-Phenylbis(trifluoromethanesulfonimide); 1,1,1-trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide; 1,1,1-Trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide; 1,1,1-三氟-N-苯基-N-[(三氟甲基)磺酰基]甲磺酰胺; N,N-双(三氟甲磺酰基)苯胺; N-苯基-三氟甲磺酰亚胺; N-苯基双(三氟甲磺酰)亚胺; N-苯基双(三氟甲烷磺酸亚胺); N-苯基双(三氟甲磺酰亚胺)

Database IDs

• CAS Number: 37595-74-7
• MDL Number: MFCD00000404
• Beilstein Number: 1269141
• PubChem SID: 160975425; 24887270; 24857826
• PubChem CID: 142176

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.0468535
• LogD (pH = 7.4): 4.0468535
• Log P: 4.0468535
• Molar Refractivity: 56.8089 cm^3
• Polarizability: 23.162031 Å^3
• Polar Surface Area: 71.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 100-102 °C; 100-102 °C(lit.); 100-102°C; 101-102°C; 102 - 104°C
• Hydrophobicity(logP): 4.825

Safety Information

• Storage Warning: IRRITANT; Irritant; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC); 95%; 97%; 98%; 99%
• Linear Formula: C6H5N(SO2CF3)2

DETAILS

Sigma Aldrich - 295973

Application
Mild triflating reagent.6,7,8
Used recently to convert a ketone to an enol triflate with KHMDS (324671) and thence an olefin with Pd(PPh3)4 (216666) and Bu3SnH (234788).
Acts as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes1Reactant for: Synthesis of amphoteric alpha-boryl aldehydes2 Enantioselective synthesis of core ring skeleton of leucosceptroids A-D3 Stereoselective synthesis of monoamine reuptake inhibitor NS9544 acetate4 Stereoselective sulfoxidation5
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 78175

Other Notes
Stable, crystalline and easy-to-handle triflating agent, useful for the triflation of phenols and amines (especially aliphatic secondary amines; aromatic secondary amines do not react)6; For the preparation of triflones7; For the preparation of enol triflates from ketones8
Packaging
5, 25, 50 g in glass bottle
Application
Acts as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes1Reactant for: Synthesis of amphoteric alpha-boryl aldehydes2 Enantioselective synthesis of core ring skeleton of leucosceptroids A-D3 Stereoselective synthesis of monoamine reuptake inhibitor NS9544 acetate4 Stereoselective sulfoxidation5

REFERENCES

• Convenient reagent for preparation of triflates of phenols and amines: Tetrahedron Lett., 4607 (1973); Org. Lett., 4, 1231 (2002); or of enol triflates from carbonyl compounds: Tetrahedron Lett., 24, 979 (1983); J. Org. Chem., 51, 277 (1986). For discussion of the reactivity of triflates, see Trifluoromethanesulfonic anhydride, A11767.