CRYSTALLOGRAPHIC AND STRUCTURAL ANALYSIS OF N-O-DIMETHYLHYDROXYLAMINE HYDROCHLORIDE

Crystallographic and Structural Analysis of N-O-Dimethylhydroxylamine Hydrochloride

Crystallographic and Structural Analysis of N-O-Dimethylhydroxylamine Hydrochloride

Blog Article

N,O-Dimethylhydroxylamine Hydrochloride: A Key Intermediate for Precision Ketone Synthesis

Chemical Name: N,O-Dimethylhydroxylamine Hydrochloride
CAS Number: 6638-79-5
Molecular Formula: C₂H₈ClNO
Synonyms: DMHA·HCl, Dimethylhydroxylamine HCl

Overview

In modern organic synthesis, reagent choice can make the difference between an average yield and a breakthrough discovery. One such high-impact reagent is N,O-Dimethylhydroxylamine hydrochloride, a stable and versatile intermediate best known for its critical role in forming Weinreb amides. With applications ranging from ketone synthesis to complex pharmaceutical development, DMHA·HCl is a staple in synthetic laboratories worldwide.

What Is N,O-Dimethylhydroxylamine Hydrochloride?

N,O-Dimethylhydroxylamine hydrochloride is a hydrochloride salt of dimethylhydroxylamine, offering enhanced shelf stability, ease of handling, and solubility compared to its free base form. The molecule features a nitrogen and oxygen methylated hydroxylamine core, which is essential for its unique reactivity profile.

Key Properties:

  • Appearance: White to off-white crystalline powder

  • Solubility: Soluble in water, methanol, ethanol, and other polar solvents

  • Stability: Hygroscopic, but stable under recommended storage conditions

Core Applications

1. Weinreb Amide Formation

Perhaps the most celebrated use of DMHA·HCl is in the synthesis of Weinreb amides. These intermediates are crucial for regioselective ketone synthesis. When treated with organolithium or Grignard reagents, Weinreb amides reliably deliver ketones—avoiding unwanted over-addition to alcohols, a common problem in carbonyl chemistry.

2. Pharmaceutical and Agrochemical Synthesis

In drug development, selective carbonyl transformations are fundamental. DMHA enables predictable, scalable access to key ketone motifs and heterocycles found in:

  • Anticancer agents

  • CNS-active compounds

  • Antiviral molecules

3. Fine Chemicals and Advanced Intermediates

DMHA·HCl is also employed in:

  • Selective acylation reactions

  • Preparation of oxime derivatives

  • Peptide coupling strategies, where control over amide bond formation is critical

Advantages Over Other Amines

Feature DMHA·HCl Traditional Amines
Reactivity control ✅ Excellent ❌ Often too reactive
Product selectivity ✅ High (via Weinreb amide) ❌ Over-addition common
Stability ✅ Stable salt form ❌ Often sensitive

Handling & Safety

While generally considered safe with appropriate precautions, DMHA·HCl is an irritant and should be handled with gloves and eye protection. Ensure proper ventilation, and consult the Material Safety Data Sheet (MSDS) for full safety guidelines.

Storage: Store in a cool, dry place, tightly sealed to avoid moisture absorption.

Conclusion

Whether you're working on targeted drug synthesis, fine chemical intermediates, or academic research, N,O-Dimethylhydroxylamine hydrochloride is an indispensable reagent that offers both precision and versatility. Its ability to enable clean ketone formation makes it a cornerstone in any synthetic chemist’s arsenal.

If you're sourcing this compound for your lab or manufacturing needs, be sure to prioritize high-purity, lab-grade material from a trusted supplier to ensure reproducible results.

Report this page