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

A17469 N,O-Dimethylhydroxylamine hydrochloride, 98%

Número CAS
6638-79-5
Nombre Alternativo

Tamaño Precio ($) Cantidad Disponibilidad
5g 38,20
25g 101,00
100g 270,00
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N,O-Dimethylhydroxylamine hydrochloride, 98%

MDL
MFCD00012485
EINECS
229-642-1

Propiedades químicas

Fórmula
CH3ONHCH3•HCl
Peso molecular
97.55
Punto de fusión
112-115°
Sensibilidad
Hygroscopic
Solubilidad
Soluble in water, dimethyl sulfoxide and methanol.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H315-H319-H335

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

Indicaciones de precaución: P260-P201-P280g-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. 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.

Otras referencias

Beilstein
3650353
Código de tarifa arancelaria unificado
2928.00
TSCA
Yes

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