[A17469] CAS 6638-79-5 | N,O-Dimethylhydroxylamine hydrochloride, 98%

CAS : 6638-79-5
MDL : MFCD00012485
EINECS : 229-642-1

Chemical Properties

Formula : CH3ONHCH3•HCl
Formula weight : 97.55
Melting Point : 112-115°
Sensitivity : Hygroscopic. Store under Nitrogen. Ambient temperatures.
Form : Crystalline powder
Solubility : Soluble in water, dimethyl sulfoxide and methanol.

Literature References

The N-methoxy-N-methylamides (Weinreb amides) of carboxylic acids, N-protected amino acids and peptides are readily prepared from the acid chloride or mixed anhydride, or from the acid in the presence of 2-Chloro-1-methyl­pyridinium iodide, A12820: Synth. Commun., 25, 1277 (1995); or BOP Reagent (1H-Benzotriazol-1-yl­oxytris(dimethyl­amino)­phosphonium hexafluorophosphate, A16140): J. Org. Chem., 61, 4999 (1996). The products undergo a number of useful transformations, e.g.: Reaction with Grignard or organolithium reagents gives ketones: Tetrahedron Lett., 22, 3815 (1981). Reduction with Lithium aluminum hydride, A18116, gives the aldehyde: Synthesis, 676 (1983). For subsequent conversion of Boc-amino acid derived aldehydes and ketones to pyrrole derivatives, see: J. Org. Chem., 61, 4999 (1996). Coupling with alkyl acetoacetates gives ß δ -diketo esters: Tetrahedron Lett., 29, 6467 (1988). For conversion to ɑ -diketones or ɑ -keto esters, see: J. Org. Chem., 54, 3913 (1989).

Applications

N,O-Dimethylhydroxylamine hydrochloride is used as a reagent in the preparation of 2-acyloxazoles from 2-oxazolemagnesium chloride and N-methoxy-N-methyl-3-oxo-butyramide from diketene. It is also used in amide coupling reactions to form Weinreb amides, which are useful in the Weinreb ketone synthesis. In addition, it is used in the preparation of an inhibitor of the NLS-derived BC peptides.

Grade Specifications

GHS Hazard and Precautionary Statements

Hazard Statements : H315-H319-H335Causes skin irritation.Causes serious eye irritation.May cause respiratory irritation.
Precautionary Statements : P261-P305+P351+P338-P302+P352-P321-P405-P501aAvoid breathing dust/fume/gas/mist/vapours/spray.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.IF ON SKIN: Wash with plenty of soap and water.Specific treatment (see label).Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.Other References:Beilstein: 3650353