N,O-Dimethylhydroxylamine
Chemical compound
From Wikipedia, the free encyclopedia
N,O-Dimethylhydroxylamine is an organic compound with the chemical formula CH3NHOCH3. Its structure is H3C−NH−O−CH3. It is a colorless liquid. It is a methylated hydroxylamine used to form so called 'Weinreb amides' for use in the Weinreb ketone synthesis.[3] It is commercially available as its hydrochloride salt (methoxy(methyl)ammonium chloride [CH3O(CH3)NH2]+Cl−).[1]
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| Names | |
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| Preferred IUPAC name
N-Methoxymethanamine | |
| Other names
Methoxymethylamine; Methylmethoxyamine; HNMeOMe | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.012.960 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C2H7NO | |
| Molar mass | 61.084 g·mol−1 |
| Appearance | Colorless liquid[2] |
| Melting point | −97 °C (−143 °F; 176 K)[3] Hydrochloride salt: 112 to 115 °C (234 to 239 °F; 385 to 388 K) |
| Boiling point | 43.2 °C (109.8 °F; 316.3 K)[3] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Serious eye irritation |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[3]
Applications
Final products containing N,O-Dimethylhydroxylamine include the following: linuron, monolinuron, metobromuron, metobenzuron, chlorbromuron & sarecycline.