N,O-Dimethylhydroxylamine HCl: A Key Weinreb Amine Derivative
N,O-Dimethylhydroxylamine HCl: A Key Weinreb Amine Derivative
Blog Article
N,O-Dimethylhydroxylamine Hydrochloride: A Small Reagent Powering Precision in Synthesis
In the meticulous world of organic chemistry, where efficiency and selectivity are paramount, certain reagents quietly outperform expectations. N,O-Dimethylhydroxylamine hydrochloride (DMHA HCl) is one such compound — a seemingly simple molecule that plays a crucial role in complex synthetic pathways, especially in pharmaceutical and fine chemical industries.
???? Chemical Identity & Properties
Name: N,O-Dimethylhydroxylamine hydrochloride
Chemical Formula: C₂H₈ClNO
Molar Mass: 97.55 g/mol
CAS Number: 6638-79-5
Appearance: White to off-white crystalline solid
Solubility: Freely soluble in water and polar organic solvents
Stability: Stable under standard storage; hygroscopic
⚗️ Synthetic Utility: The Power Behind Weinreb Amides
DMHA HCl is best known for its role in the formation of Weinreb amides — a key class of intermediates that allow controlled mono-addition of organometallic reagents to carbonyl compounds.
Why it matters:
When acid chlorides or esters are treated with N,O-dimethylhydroxylamine, the resulting Weinreb amides can react with Grignard or organolithium reagents to yield ketones selectively, avoiding over-reduction to alcohols — a common issue with direct addition methods.
This precision makes DMHA HCl indispensable for multistep synthesis, especially in target-oriented synthesis of APIs (active pharmaceutical ingredients), agrochemicals, and complex natural products.
???? Applications Across Industries
1. Pharmaceutical Development
DMHA HCl is employed in the synthesis of:
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Corticosteroid intermediates
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CNS-active compounds
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Ketone-containing drug scaffolds
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Custom libraries for drug discovery
2. Agrochemicals & Fine Chemicals
In crop protection and materials chemistry, DMHA-derived Weinreb amides provide a clean route to structurally diverse ketones — often under mild, scalable conditions.
3. Process Chemistry & Scale-Up
Because DMHA HCl is a bench-stable crystalline salt, it’s ideal for use in GMP environments. Its non-volatile nature and high purity make it safer and easier to handle in pilot and production-scale chemistry.
???? Safety, Handling, and Storage
DMHA HCl is relatively low in acute toxicity but should be handled with standard laboratory precautions.
Recommendations:
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Use in a fume hood with gloves and eye protection
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Avoid inhalation or contact with skin
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Store in a cool, dry, tightly sealed container, protected from moisture
Refer to your supplier's SDS (Safety Data Sheet) for detailed hazard and first aid information.
???? Availability & Sourcing
DMHA HCl is readily available from reputable chemical suppliers such as:
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Sigma-Aldrich
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TCI Chemicals
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Alfa Aesar
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Merck
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Various specialty CROs and bulk manufacturers
It is typically sold in purities of ≥98% and packaged in moisture-resistant containers. For large-scale applications, custom synthesis or bulk supply agreements are common.
???? Final Thoughts: Why This Reagent Still Matters
In modern organic synthesis, especially in the pharmaceutical pipeline, predictability and efficiency are everything. N,O-Dimethylhydroxylamine hydrochloride delivers both — enabling chemists to build complex molecules with confidence and control. Its role in Weinreb amide formation may seem specialized, but its impact is foundational.
If you're involved in ketone synthesis, drug development, or building a robust synthetic route — DMHA HCl is more than just a helper. It’s a strategic enabler.
Looking to optimize a Weinreb amide synthesis? Need help with reagent selection for your next synthetic campaign? Reach out or follow our blog for more deep-dives into smart chemistry solution
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