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L12531 N-Phenylbis(trifluoromethanesulfonimide), 99%

CAS Number
37595-74-7
Synonyms
N,N-Bis(trifluoromethanesulfonyl)aniline
Phenyl triflimide

Stock No. Size Price ($) Quantity Availability
L12531-03 1g 22.60
L12531-06 5g 57.50
L12531-14 25g 244.00
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N-Phenylbis(trifluoromethanesulfonimide), 99%

MDL
MFCD00000404

Chemical Properties

Formula
(CF3SO2)2NC6H5
Formula Weight
357.25
Melting point
100-102°
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
Soluble in methanol. Slightly soluble in chloroform and ethyl acetate.

Applications

N-Phenylbis(trifluoromethanesulfonimide) acts as a mild triflating reagent as well as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes. It is also employed as a reactant for the preparation of amphoteric alfa-boryl aldehydes. It plays an important role in the enantioselective synthesis of the core ring skeleton of leucosceptroids A-D and in steroselective sulfoxidation. Further, it is used in the enantioselective synthesis of beta-amino acids through the Mannich reaction. In addition to this, it is used in the preparation of sphingosine 1-phosphate-1 receptor agonists.

Notes

Hygroscopic. Store in a cool place. Moisture sensitive. Incompatible with strong oxidizing agents.

Literature 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.

Konoura, K.; Fujii, H.; Imaide, S.; Gouda, H.; Hirayama, S.; Hirono, S.; Nagase, H. Transformation of naltrexone into mesembrane and investigation of the binding properties of its intermediate derivatives to opioid receptors. Bioorg. Med. Chem. 2015, 23 (3), 439-448.

Chirkin, E.; Atkatlian, W.; Porée, F. H. Chapter One-The Securinega Alkaloids. Alkaloids Chem. Biol. 2015, 74, 1-120.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1269141
Harmonized Tariff Code
2935.90
TSCA
No

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