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295973

Sigma-Aldrich

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

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About This Item

Linear Formula:
C6H5N(SO2CF3)2
CAS Number:
37595-74-7
Molecular Weight:
357.25
Beilstein/REAXYS Number:
1269141
MDL number:
MFCD00000404
UNSPSC Code:
12352002
PubChem Substance ID:
24857826
NACRES:
NA.22

Quality Level

200

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

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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).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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José M Mejía-Oneto et al.
Organic letters, 8(15), 3275-3278 (2006-07-14)
[Structure: see text] A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of
Tetrahedron, 47, 3485-3485 (1991)
Journal of the American Chemical Society, 112, 8578-8578 (1990)
Chemistry Letters (Jpn), 7, 1313-1313 (1989)

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