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N,O-Dimethylhydroxylamine

N,O-Dimethylhydroxylamine
Structual formula of N,O-dimethylhydroxylamine
Ball-and-stick model of the N,O-dimethylhydroxylamine molecule
Names
IUPAC name
N-Methoxymethanamine
Other names
Methoxymethylamine; Methylmethoxyamine; HNMeOMe
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.960
PubChem CID
Properties
C2H7NO
Molar mass 61.08 g·mol−1
Melting point −97 °C (−143 °F; 176 K)

Hydrochloride salt: 112 to 115 °C (234 to 239 °F; 385 to 388 K)
Boiling point 43.2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

N,O-Dimethylhydroxylamine is a methylated hydroxylamine used to form so called 'Weinreb amides' for use in the Weinreb ketone synthesis. It is commercially available as its hydrochloride salt.

It may be prepared by reacting ethyl chloroformate (or similar) with hydroxylamine followed by treatment with a methylating agent such as dimethyl sulfate. The N,O-dimethylhydroxylamine is then liberated by acid hydrolysis followed by neutralization.



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