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78175

Sigma-Aldrich

N-Phenyl-bis(trifluoromethanesulfonimide)

≥98.0% (HPLC)

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:
Molecular Weight:
357.25
Beilstein:
1269141
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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