Misplaced Pages

N,O-Dimethylhydroxylamine

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
N,O-Dimethylhydroxylamine
Structural formula of N,O-dimethylhydroxylamine
Ball-and-stick model of the N,O-dimethylhydroxylamine molecule
Names
Preferred IUPAC name N-Methoxymethanamine
Other names Methoxymethylamine; Methylmethoxyamine; HNMeOMe
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.960 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H7NO/c1-3-4-2/h3H,1-2H3Key: KRKPYFLIYNGWTE-UHFFFAOYSA-N
  • InChI=1/C2H7NO/c1-3-4-2/h3H,1-2H3Key: KRKPYFLIYNGWTE-UHFFFAOYAP
SMILES
  • CNOC
Properties
Chemical formula C2H7NO
Molar mass 61.084 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

See also

References

  1. ^ N,O-Dimethylhydroxylamine hydrochloride at Sigma-Aldrich
  2. ^ 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. ISBN 0471936235.
Categories: