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78175

Sigma-Aldrich

N-Phenyl-bis(trifluoromethanesulfonimide)

≥98.0% (HPLC)

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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:
57652731
NACRES:
NA.22

Quality Level

200

Assay

≥98.0% (HPLC)

form

crystals

mp

100-102 °C (lit.)
100-102 °C

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

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); For the preparation of triflones; For the preparation of enol triflates from ketones

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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J.B. Hendrickson et al.
Tetrahedron, 31, 2517-2517 (1975)
J.B. Hendrickson et al.
The Journal of Organic Chemistry, 42, 3875-3875 (1977)
W.J. Scott et al.
Accounts of Chemical Research, 21, 47-47 (1988)

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