4-Methylmorpholine / NMM (CAS 109-02-4): Tertiary Amine Base for Peptide Coupling, Oxidation, and Polymerization
N-Methylmorpholine (NMM) is a medium-strength tertiary amine whose hydrophilic morpholine core makes it water-soluble, readily removable by extraction, and mild toward sensitive substrates. In process chemistry it is best known as the base of peptide-amide coupling protocols and as the precursor to N-methylmorpholine-N-oxide (NMO), the stoichiometric oxidant of osmium-catalyzed dihydroxylation.
Chemical Identity and Key Properties
| Property | Value |
|---|---|
| CAS Number | 109-02-4 |
| Molecular Formula | C5H11NO |
| Molecular Weight | 101.08 g/mol |
| Density | 0.9 @25 °C |
| Typical Purity | 99% |
Peptide and Amide Coupling
EDC/NMM (or EDC/Oxyma variants) remains a standard aqueous-organic route for fragment coupling and conjugate preparation; the base buffers the acidic by-products while extracting cleanly into aqueous washes — a practical advantage over Et3N in workup design.
NMO and Oxidation Chemistry
Oxidation of NMM with hydrogen peroxide yields NMO, the recyclable oxidant paired with catalytic OsO4 in Upjohn dihydroxylation of alkenes; the NMM supply chain is therefore coupled to fine-chemical oxidation capacity.
Catalysis and Other Applications
As a polymerization-catalyst base, NMM appears in polyurethane foaming; as a general base, it supports sulfonylation, silylation, and phase-transfer protocols where a moderately nucleophilic tertiary amine is tolerated.
Handling Notes
NMM is a flammable, hygroscopic liquid with a penetrating amine odor; it absorbs CO2 and moisture in storage. Keep sealed, dry, and ventilated; verify water content before use in water-sensitive steps.
Frequently Asked Questions
What purity is available for NMM?
Typical catalog material is ≥99% with water below 0.2% for synthesis-grade; CoreyChem can supply additional drying to meet tighter moisture limits.
Can NMM be supplied in bulk?
Drums and larger formats are standard; custom packaging arrangements available on request.
Does CoreyChem supply NMO as well?
Yes — N-methylmorpholine-N-oxide and related morpholine derivatives are available with full documentation.
Source from CoreyChem
CoreyChem supplies 4-Methylmorpholine (CAS 109-02-4) with lot-specific COA and MSDS documentation. Custom synthesis, higher purity grades, and bulk packaging are available on request — contact our technical team with your target specification and quantity for current lead time and pricing.