922684
N-Methyl-O-nosylhydroxylammonium triflate
Synonym(s):
NsONH2Me·OTf
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About This Item
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form
powder
Quality Level
mp
79.8-109.2 °C (Decomp.)
functional group
amine
fluoro
nitro
sulfonic acid
triflate
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.
Signal Word
Danger
Hazard Statements
Precautionary 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
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Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination.
Organic Letters, 23, 1422-1426 (2021)
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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