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Key Documents

922684

Sigma-Aldrich

N-Methyl-O-nosylhydroxylammonium triflate

Synonym(s):

NsONH2Me·OTf

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About This Item

Empirical Formula (Hill Notation):
C8H9F3N2O8S2
CAS Number:
Molecular Weight:
382.29
UNSPSC Code:
12352101

form

powder

Quality Level

mp

79.8-109.2 °C (Decomp.)

storage temp.

−20°C

Application

N-Methyl-O-nosylhydroxylammonium triflate is a reagent used in iron catalyzed synthesis of N-methylamines from simple arenes. This reagent can be used to form various aryl amines without the use of precious metal catalysts, harsh conditions or complex multi-step syntheses, and represents a more robust alternative to other coupling methods of forming sp2 C-N bonds.

Pictograms

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Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Org. Perox. C - Skin Irrit. 2

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination.
Falk, et al.
Organic Letters, 23, 1422-1426 (2021)
Eric Falk et al.
Organic letters, 23(4), 1422-1426 (2021-02-06)
We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes.

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