N-Methylmorpholine (NMM) is a cyclic tertiary amine and aprotic solvent widely used as a versatile base catalyst and reaction medium in pharmaceutical synthesis, peptide chemistry, and polyurethane production. Thanks to its moderate basicity (pKa of conjugate acid≈7.4), low nucleophilicity, and excellent solubility in both water and organic solvents, NMM is the preferred substitute for triethylamine (TEA) and N,N-diisopropylethylamine (DIPEA) in many sensitive reactions.

Synonyms:
4-Methylmorpholine; 1-Methylmorpholine; N-Methyl morphofine; N-Methyl Morpholine; Methylmorpholine; Methyl Morpholine; N-Morpholine

 

Technical Specifications

ITEMS SPECIFICATIONS
Appearance Colorless transparent liquid
Purity ≥99.6%
Moisture ≤0.10%

 

Packaging and Storage

  • 180kgs galvanized iron drum, 14.4MT/FCL with pallets.
  • Store in cool, well-ventilated area away from strong oxidizers and acids.

 

Main Applications of N-Methylmorpholine (NMM)

Polyurethane Catalysis:
Tertiary amine catalyst (blow catalyst) in flexible and rigid polyurethane foam production.
Promotes the water–isocyanate “blowing” reaction more than the gelling reaction, helping control foam rise and cell structure.
Often used in combination with other catalysts (e.g., with tin catalysts like dibutyltin dilaurate).

Pharmaceutical Intermediate & Catalyst:
Base and catalyst in numerous pharmaceutical syntheses (e.g., production of antibiotics, anticancer drugs, antifungals).
Used in reactions requiring a moderately strong, non-nucleophilic base (pKa of conjugate acid ≈ 7.4).
Solvent or co-solvent in reactions sensitive to stronger bases like triethylamine or DBU.

Solvent and Extraction Agent:
Polar aprotic solvent in certain reactions.
Used in solvent extraction processes (e.g., extraction of aromatic hydrocarbons or metal ions).

Peptide Synthesis:
Primary coupling reagent activator in solid-phase and solution-phase peptide synthesis.
Used with carbodiimides (DCC, DIC, EDC) to form active esters, suppressing racemization better than additives like HOBt or HOAt in many cases.
Preferred in automated peptide synthesizers because it is less allergenic and has lower toxicity compared to HOBt.

Corrosion Inhibition:
Component of some corrosion inhibitor formulations for oilfield and industrial water systems (forms protective films on metal surfaces).

Rubber and Polymer Chemistry:
Vulcanization accelerator for chloroprene rubber (Neoprene).
Catalyst in silicone and polyurethane elastomers.

Agrochemical Synthesis:
Intermediate or base in the synthesis of certain herbicides, insecticides, and fungicides.

 

Frequently Asked Questions (FAQs)

Q: Can N-Methylmorpholine (NMM) replace triethylamine (TEA) in peptide coupling reactions?
A: Yes. NMM is widely used as a superior alternative to TEA because it produces fewer side reactions, has better solubility properties, and forms water-soluble salts that are easier to remove.

Q: Does NMM have any odor?
A: It has a mild amine-like odor, significantly weaker than triethylamine or morpholine.

Q: Does N-Methylmorpholine (NMM) react with CO₂ in air?
A: Yes, it slowly absorbs CO₂ forming a crystalline carbamate salt. Use nitrogen blanketing for long-term storage of opened containers.

Q: What is the recommended storage condition?
A: Store in a cool, well-ventilated area away from sources of ignition and strong acids. Keep containers tightly closed under inert gas when possible.

 

Where can I buy high-quality N-Methylmorpholine (NMM)?

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