295973

N-Phenyl-bis(trifluoromethanesulfonimide)

99%

• Synonym(s): 1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide, N,N-Bis(trifluoromethylsulfonyl)aniline, N-Phenyl-trifluoromethanesulfonimide, NSC 240874, Phenyl triflimide
• Linear Formula: C₆H₅N(SO₂CF₃)₂
• CAS Number: 37595-74-7
• Molecular Weight: 357.25
• Beilstein: 1269141
• MDL number: MFCD00000404
• UNSPSC Code: 12352002
• PubChem Substance ID: 24857826
• NACRES: NA.22

Properties

• Assay: 99%
• form: solid
• mp: 100-102 °C (lit.)
• SMILES string: FC(F)(F)S(=O)(=O)N(c1ccccc1)S(=O)(=O)C(F)(F)F
• 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
• InChI key: DIOHEXPTUTVCNX-UHFFFAOYSA-N

Description

Application

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

Mild triflating reagent.

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).

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves