REACTIVITY PROFILE OF N,O-DIMETHYLHYDROXYLAMINE HCL

Reactivity Profile of N,O-Dimethylhydroxylamine HCl

Reactivity Profile of N,O-Dimethylhydroxylamine HCl

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N,O-Dimethylhydroxylamine Hydrochloride: A Precision Reagent Driving Modern Organic Synthesis


N,O-Dimethylhydroxylamine HCL

In the era of high-performance pharmaceuticals and tailored fine chemicals, precision in molecular construction is paramount. Among the essential tools enabling that precision is N,O-Dimethylhydroxylamine hydrochloride (DMHA HCl) — a small, crystalline reagent with outsized impact in ketone synthesis, intermediate development, and scale-up chemistry.


Often underestimated due to its simplicity, DMHA HCl is a cornerstone in the synthesis of Weinreb amides — a class of intermediates that deliver unmatched control in carbon–carbon bond formation.






???? Molecular Overview









































Property Details
Chemical Name N,O-Dimethylhydroxylamine hydrochloride
Formula C₂H₈ClNO
Molecular Weight 97.55 g/mol
CAS Number 6638-79-5
Appearance White to off-white crystalline powder
Solubility Freely soluble in water and polar solvents
Stability Hygroscopic; stable under inert storage




DMHA HCl is the hydrochloride salt of N,O-dimethylhydroxylamine, offering increased shelf-stability, reduced volatility, and ease of handling — especially crucial in industrial and regulated environments.






???? Synthetic Utility: The Weinreb Advantage


The formation of Weinreb amides using DMHA HCl is one of the most elegant and reliable strategies in ketone synthesis. When reacted with acid chlorides, anhydrides, or esters, DMHA yields amides that undergo selective mono-addition with organometallic reagents — producing ketones with minimal by-products.



Key Reaction:



text



Acid chloride + MeN(OMe)H·HCl → Weinreb amide → R–C(=O)–R′ (via Grignard or organolithium)




Why Chemists Choose Weinreb Amides:




  • Avoids over-addition (common with esters and acid chlorides)




  • Excellent chemoselectivity




  • Scalable and predictable




  • Compatible with Grignards, lithium reagents, and other nucleophiles




DMHA HCl is the preferred form of this reagent due to its solid-state stability and ease of purification — perfect for both discovery and GMP environments.






???? Applications in Pharma, Fine Chemicals & Beyond


DMHA HCl plays a central role in diverse sectors:



1. Pharmaceutical Synthesis


Used to construct:





  • Aryl and heteroaryl ketones in CNS and anti-inflammatory drugs




  • Steroidal frameworks




  • Alkaloid intermediates




  • Building blocks in structure-activity relationship (SAR) campaigns




2. Agrochemicals & Specialty Materials


Enables synthesis of:





  • Herbicide and fungicide scaffolds




  • UV-absorbing compounds




  • Functionalized ketones for polymer additives




3. Process Development & Scale-Up


Ideal for:





  • Pilot plant synthesis and GMP-compliant manufacturing




  • Route scouting and kilolab work




  • Optimization of reaction efficiency, yield, and safety







???? Practical Advantages





























Feature Benefit
Crystalline HCl salt Easy to weigh and store
Non-volatile Safer for large-scale operations
Broad solvent compatibility Flexible across diverse conditions
High selectivity Reduces side-products and purification burdens




DMHA HCl is especially valued for its ability to be used in situ or pre-formed as a free base, offering flexibility across research and industrial settings.






⚠️ Safety & Handling


DMHA HCl is relatively low in toxicity, but as a reactive amine, it requires standard chemical precautions:





  • Store in a dry, tightly sealed container




  • Handle with gloves and eye protection




  • Avoid inhalation or prolonged contact




  • Use in a well-ventilated area or fume hood




???? Always consult your supplier’s SDS for full safety guidance.






???? Commercial Availability


Available from leading chemical suppliers:





  • Milligram to bulk-scale packaging




  • Purity typically ≥98%




  • Custom synthesis and documentation available for regulated markets




Suppliers include:





  • MilliporeSigma / Merck




  • TCI America




  • Alfa Aesar




  • Thermo Fisher




  • Multiple CROs offering GMP supply




For procurement teams and sourcing chemists, DMHA HCl offers reliability, consistency, and favorable regulatory positioning for route approval.






???? Final Thoughts: Small Molecule, Strategic Value


While not flashy, N,O-Dimethylhydroxylamine hydrochloridehttps://www.ketonepharma.com/product/n-o-dimethylhydroxylamine is a strategic reagent. It sits quietly on shelves, but enables bold strides in synthetic innovation — from milligram benchwork to ton-scale production.


Its role in Weinreb amide formation is now a textbook staple — but its relevance is only growing, especially as process chemistry and targeted synthesis demand ever-tighter control over functional group transforWhether mations.





Whether you're:optimizing a synthetic route or scaling a clinical candidate, DMHA HCl isn’t just a reagent — it’s a precision tool.






???? Need DMHA HCl for Your Next Project?


Building a ketone-rich scaffold






  • Developing a scalable synthesis route




  • Procuring cGMP-compliant raw materials




…DMHA HCl is available in research, pilot, and production scale.


???? Contact our sourcing team or request a custom quote for bulk quantities.

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