N,O-Dimethylhydroxylamine
N,O-Dimethylhydroxylamine is a methylated hydroxylamine used to form so called 'Weinreb amides' for use in the Weinreb ketone synthesis.[2] It is commercially available as its hydrochloride salt.[1]
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| Names | |
|---|---|
| IUPAC name
N-Methoxymethanamine | |
| Other names
Methoxymethylamine; Methylmethoxyamine; HNMeOMe | |
| Identifiers | |
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| ChemSpider | |
| ECHA InfoCard | 100.012.960  |
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| Properties | |
| C2H7NO | |
| Molar mass | 61.084 g·mol−1 |
| Melting point | −97 °C (−143 °F; 176 K)[2] Hydrochloride salt: 112 to 115 °C (234 to 239 °F; 385 to 388 K) |
| Boiling point | 43.2 [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 | |
Synthesis
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.[2]
See also
- Methoxyamine
- N-methylhydroxylamine
References
- N,O-Dimethylhydroxylamine hydrochloride at Sigma-Aldrich
- Weinreb, Steven M.; Folmer, James J.; Ward, Timothy R.; Georg, Gunda I. (2006). "N,O-Dimethylhydroxylamine". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd341.pub2.
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