N,O-Dimethylhydroxylamine

N,O-Dimethylhydroxylamine^[1]
Names
	Preferred IUPAC name N-Methoxymethanamine
	Other names Methoxymethylamine; Methylmethoxyamine; HNMeOMe
Identifiers
CAS Number	1117-97-1 ; 6638-79-5 (HCl) ;
3D model (JSmol)	Interactive image;
ChemSpider	13596 ;
ECHA InfoCard	100.012.960
PubChem CID	14232;
UNII	783670HYEO ;
CompTox Dashboard (EPA)	DTXSID5051577 ;
	InChI InChI=1S/C2H7NO/c1-3-4-2/h3H,1-2H3 Key: KRKPYFLIYNGWTE-UHFFFAOYSA-N ; InChI=1/C2H7NO/c1-3-4-2/h3H,1-2H3 Key: KRKPYFLIYNGWTE-UHFFFAOYAP;
	SMILES CNOC;
Properties
Chemical formula	C2H7NO
Molar mass	61.084 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). verify (what is ?) Infobox references

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]

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]

^ ^a ^b N,O-Dimethylhydroxylamine hydrochloride at Sigma-Aldrich
^ ^a ^b ^c ^d 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.