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

A17469 N,O-Dimethylhydroxylamine hydrochloride, 98%

Numéro de CAS
6638-79-5
Synonymes

Conditionnement Prix ($) Quantité Disponibilité
5g 38,20
25g 101,00
100g 270,00
Ajouter au panier Ajouter au devis en vrac Afficher l'article

N,O-Dimethylhydroxylamine hydrochloride, 98%

MDL
MFCD00012485
EINECS
229-642-1

Propriétés chimiques

Formule
CH3ONHCH3•HCl
Poids moleculaire
97.55
Point de fusion
112-115°
Sensibilité
Hygroscopic
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Beilstein
3650353
Code tarifaire harmonisé
2928.00
TSCA
Yes

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Analytique et matériel de laboratoire