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A17469 N,O-Dimethylhydroxylamine hydrochloride, 98%

CAS Number
6638-79-5
Synonyms

Stock No. Size Price ($) Quantity Availability
A17469-06 5g 39.40
A17469-14 25g 105.00
A17469-22 100g 281.00
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N,O-Dimethylhydroxylamine hydrochloride, 98%

MDL
MFCD00012485
EINECS
229-642-1

Chemical Properties

Formula
CH3ONHCH3•HCl
Formula Weight
97.55
Melting point
112-115°
Storage & Sensitivity
Hygroscopic. Store under Nitrogen. Ambient temperatures.
Solubility
Soluble in water, dimethyl sulfoxide and methanol.

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.

Notes

Hygroscopic. Store in a cool place. Incompatible with strong oxidizing agents.

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).

Burk, M.; Wilson, N.; Herzon, S. B. Multigram synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-l-pyrrolosamine. Tetrahedron Lett. 2015, 56 (23), 3231-3234.

Prosser, A. R.; Liotta, D. C. One-pot transformation of esters to analytically pure ketones: Methodology and application in process development. Tetrahedron Lett. 2015, 56 (23), 3005-3007.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P264b-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse.

Other References

Beilstein
3650353
Harmonized Tariff Code
2928.00
TSCA
Yes

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