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6638-79-5 - N,O-Dimethylhydroxylamine hydrochloride, 98% - A17469 - Alfa Aesar

A17469 N,O-Dimethylhydroxylamine hydrochloride, 98%

CAS-Nummer
6638-79-5
Synonyme

Größe Preis ($) Menge Verfügbarkeit
5g 38,20
25g 101,00
100g 270,00
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

N,O-Dimethylhydroxylamine hydrochloride, 98%

MDL
MFCD00012485
EINECS
229-642-1

Chemische Eigenschaften

Formel
CH3ONHCH3•HCl
Molmasse
97.55
Schmelzpunkt
112-115°
Sensitivität
Hygroscopic
Löslichkeit
Soluble in water, dimethyl sulfoxide and methanol.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
3650353
Harmonized Tariff Code
2928.00
TSCA
Yes

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