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N,O-Dimethylhydroxylamine hydrochloride is used as a pharmaceutical intermediate. 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.
Items | Specifications | Results |
Appearance | White to slighty-white crystalline powder | Conforms |
Identification | Conforms | |
DMHA:Water(M/M=1:9) | Colorless transparent,no suspended matter,no impurities | Conforms |
Assay(Titration) | ≥98.5% | 99.56% |
Melting Point | 112℃~116℃ | 112.4-115.8℃ |
Water | ≤0.5% | 0.25% |
Conclusion | The product conforms to the above specifications. | |
| Product parameters | |
| Cas number: | 6638-79-5 |
| Appearance: | White powder |
| Purity: | 99.0%min |
| Package details: | 1kg/foil bag, 25kg/drum |
| Brand: | Fortunachem |
N,O-Dimethylhydroxylamine hydrochloride is an organic compound with the formula (CH₃)₂NOH·HCl. It is the stable, solid hydrochloride salt of N,O-dimethylhydroxylamine, widely used as a specialized reagent in synthetic organic chemistry.
Its most important application is the formation of Weinreb amides. These are stable intermediates that allow for the controlled synthesis of ketones or aldehydes from more reactive carboxylic acid derivatives (like esters or acid chlorides).
Mechanism: It reacts with an ester or acid chloride to form a Weinreb amide. The methoxy group chelates to the lithium or magnesium cation of a Grignard or organolithium reagent, preventing over-addition and cleanly yielding a ketone after aqueous workup.
Conversion of Aldehydes to Weinreb Enamines: Useful for the equivalent of an acyl anion synthon.
Protection of Aldehydes: Transforms sensitive aldehydes into more stable derivatives for multi-step synthesis.
General N-Nucleophile: Used in various nucleophilic substitution reactions to introduce the N-methoxy-N-methyl (Weinreb) group.
Why it's preferred: It provides exceptional control in carbonyl transformations where traditional methods lead to overreaction (e.g., getting a tertiary alcohol from an ester + 2 equivalents of Grignard reagent).
Physical Form: Typically a white to off-white crystalline solid.
Safety: It is toxic, corrosive, and moisture-sensitive. It must be handled in a fume hood with appropriate personal protective equipment (PPE) due to the release of hydrochloric acid and potential toxicity of the free amine.
In summary, N,O-Dimethylhydroxylamine hydrochloride is an indispensable reagent for the controlled synthesis of ketones via Weinreb amides, a fundamental transformation in modern pharmaceutical and complex molecule synthesis.
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