N-METHYLMORPHOLINE (NMM)

N-methylmorpholine (NMM) is the organic compound with the formula O(CH2CH2)2NCH3. 
N-methylmorpholine (NMM) is a colorless liquid. 
N-methylmorpholine (NMM) is a cyclic tertiary amine. 

CAS Number: 109-02-4
Molecular Formula: C5H11NO
Molecular Weight: 101.15
EINECS Number: 203-640-0

Synonyms: NMM N-methylmorpholine (NMM), SCHEMBL2123718, PSACHCMMPFMFAJ-UHFFFAOYSA-N, NMM;N-Methyl morphofine;N-METHYLMORPHOLINE;4-METHYL-1-OXA-4-AZACYCLOHEXANE;4-METHYLMORPHOLINE;AKOS 89985;LUPRAGEN(R) N 105;1-Methylmorpholine

N-methylmorpholine (NMM) is used as a base catalyst for generation of polyurethanes and other reactions. 
N-methylmorpholine (NMM) is produced by the reaction of methylamine and diethylene glycol as well as by the hydrogenolysis of N-formylmorpholine.
N-methylmorpholine (NMM) is the precursor to N-methylmorpholine (NMM) N-oxide, a commercially important oxidant.

N-methylmorpholine (NMM), is a heterocyclic tertiary amine with the chemical formula C5H11NO, consisting of a six-membered morpholine ring in which one of the nitrogen atoms is substituted with a methyl group, and this structural configuration imparts both basicity and moderate nucleophilicity, making it a versatile reagent in organic synthesis and industrial chemistry.
N-methylmorpholine (NMM) is a colorless to pale yellow liquid under standard conditions with a characteristic amine-like odor, high volatility, and excellent miscibility with a wide range of organic solvents, including alcohols, ethers, ketones, and chlorinated hydrocarbons, which facilitates its use in homogeneous reaction media and industrial processes requiring a soluble, basic catalyst or reactant.

N-methylmorpholine (NMM) acts as a non-nucleophilic, sterically hindered base in organic reactions, enabling deprotonation, neutralization of acids, or activation of reagents without participating in unwanted side reactions, and it is also employed as a catalyst, reaction medium, or intermediate in the synthesis of polyurethanes, pharmaceuticals, agrochemicals, and specialty chemicals, where its ability to stabilize reactive intermediates and enhance reaction rates improves efficiency, yield, and selectivity in complex chemical processes.

N-methylmorpholine (NMM) colorless and transparent liquid. with characteristic odor soluble in organic solvents, miscible with water and ethanol.
N-methylmorpholine (NMM) is a colorless to pale yellow liquid organic compound featuring a six-membered heterocyclic morpholine ring in which the nitrogen atom is substituted with a methyl group, giving the molecule the chemical formula C5H11NO and a molecular weight of approximately 85.15 g/mol, which contributes to its basicity, nucleophilicity, and versatility as a chemical reagent in both laboratory and industrial applications.

N-methylmorpholine (NMM) exhibits excellent solubility in a wide range of organic solvents, including alcohols, ketones, ethers, esters, and chlorinated hydrocarbons, and partial solubility in water, which allows it to function as a reaction medium, catalyst, or co-solvent in a variety of chemical reactions, while maintaining stability under moderate temperatures and inert atmospheric conditions.
N-methylmorpholine (NMM) is a tertiary amine belonging to the morpholine family, widely used as a solvent, catalyst, and intermediate in chemical synthesis.

N-methylmorpholine (NMM) is valued for its high polarity, low volatility, and compatibility with a broad range of organic and inorganic compounds.
N-methylmorpholine (NMM)is extensively applied in pharmaceuticals, agrochemicals, polyurethane production, and specialty chemical industries.

N-methylmorpholine (NMM) is a water-white liquid with an ammonia-like odor less dense than water and insoluble in water. 
Flash point 75°F. May be moderately toxic by ingestion, inhalation and skin absorption. 
Very irritating to skin, eyes, and mucous membranes. Used as a solvent and to make pharmaceuticals.

In the industrial polymer sector, N-methylmorpholine (NMM) is often used as a catalyst in the production of polyurethane foams, coatings, and elastomers, where it facilitates the reaction between isocyanates and polyols, controlling polymer chain growth, reaction kinetics, and cross-linking density, which directly influences mechanical properties, thermal stability, and surface characteristics of the final polymer products.

In organic synthesis, N-methylmorpholine (NMM) serves as a sterically hindered, non-nucleophilic tertiary amine base, which enables it to deprotonate acidic compounds, neutralize acidic byproducts, or activate reagents without participating in undesirable side reactions, making it particularly valuable for sensitive or highly selective transformations, including esterifications, acylations, condensations, and polymerization reactions.

Melting point: −66 °C (lit.)
Boiling point: 115-116 °C (750 mm Hg, lit.)
Density: 0.92 g/mL at 25 °C (lit.)
Vapor density: >1 (vs air)
Vapor pressure: 18 mm Hg (20 °C)
Refractive index: n20/D 1.435 (lit.)
Flash point: 75 °F
Storage temp.: Store below +30 °C
Solubility: Soluble in chloroform, ethyl acetate; slightly soluble in methanol
Form: Liquid
pKa: 7.38 (at 25 °C)
Color: Clear
Specific Gravity: 0.920 (20/4 °C)
pH: 10.6 (50 g/L, H2O, 20 °C)
Explosive limit: 2.1% (V)
Viscosity: 0.87 mm2/s
Water Solubility: >500 g/L (20 °C)
Merck: 14,6277
BRN: 102719
Stability: Volatile
InChIKey: SJRJJKPEHAURKC-UHFFFAOYSA-N
LogP: -0.32 (25 °C)

N-methylmorpholine (NMM) is a heterocyclic tertiary amine with a methyl-substituted morpholine ring, known for its strong basicity, miscibility with organic solvents, and ability to act as a non-nucleophilic base or catalyst, widely used in organic synthesis, polymer production, pharmaceutical manufacturing, and specialty chemical processes, where it contributes to improved reaction efficiency, control over product formation, and enhancement of material properties in industrial and laboratory applications.
N-methylmorpholine (NMM) is a colorless liquid with a characteristic amine-like odor.

N-methylmorpholine (NMM) is miscible with water, alcohols, ketones, and hydrocarbons.
N-methylmorpholine (NMM) has high polarity, making it an effective solvent in synthesis.
N-methylmorpholine (NMM) is volatile and produces flammable vapors.

N-methylmorpholine (NMM) reacts with acids to form salts.
N-methylmorpholine (NMM) is corrosive to certain metals in the presence of moisture.
N-methylmorpholine (NMM) is stable under recommended storage conditions.

N-methylmorpholine (NMM) is biodegradable under environmental conditions.
N-methylmorpholine (NMM) exhibits low acute toxicity but requires careful handling.
N-methylmorpholine (NMM) is classified as hazardous due to flammability and irritant properties.

N-methylmorpholine (NMM) preparation method is to slowly add formaldehyde in morpholine drop by drop, under stirring add formic acid reaction, automatic reflux, and release carbon dioxide. 
After adding formic acid, heating reflux 4 ~ 5h, cooling and adding sodium hydroxide immediately distillation, collect all the fraction before the boiling point of 99 ℃, and then add sodium hydroxide in the fraction to saturation, cooling the oil layer, drying, fractional distillation, to obtain N-methylmorpholine (NMM).

Amines are chemical bases they neutralize acids to form salts plus water. 
These acid-base reactions are exothermic. 
The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. 

Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. 
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
In the polymer and polyurethane industry, N-methylmorpholine (NMM) is widely used as a catalyst to accelerate the reaction between polyols and isocyanates, controlling reaction kinetics, cross-linking density, and polymer chain growth, which directly affects the mechanical strength, elasticity, thermal stability, and surface properties of foams, elastomers, coatings, adhesives, and composite materials, making it indispensable in high-performance construction materials, furniture, automotive components, and insulation products.

Uses:
N-methylmorpholine (NMM) is extensively used as a non-nucleophilic tertiary amine base in organic synthesis, where its sterically hindered structure allows it to deprotonate acids, activate reagents, and neutralize acidic byproducts without engaging in unwanted side reactions, which makes it particularly valuable in sensitive or highly selective reactions such as esterifications, acylations, condensations, and cyclization reactions, enabling chemists to obtain high yields, high purity, and precise control over reaction pathways in pharmaceutical, agrochemical, and specialty chemical manufacturing.

In the polymer and polyurethane industries, N-methylmorpholine (NMM) functions as a catalyst that accelerates the reaction between polyols and isocyanates, facilitating controlled polymer chain growth, precise cross-linking, and optimized reaction kinetics, which directly enhances the mechanical strength, elasticity, thermal stability, and surface properties of polyurethane foams, elastomers, coatings, adhesives, and composite materials, making it essential for applications in furniture, automotive components, construction insulation, and high-performance materials.

N-methylmorpholine (NMM) is utilized in epoxy resin curing.
N-methylmorpholine (NMM) is used in adhesive and coating applications requiring amine-based hardeners.
N-methylmorpholine (NMM) is applied in specialty polymers as a curing accelerator.

N-methylmorpholine (NMM) is incorporated into textile processing as a finishing agent.
N-methylmorpholine (NMM) is used in leather treatment formulations.
N-methylmorpholine (NMM) is applied in industrial detergents and cleaners.

N-methylmorpholine (NMM) is employed in corrosion inhibitors for metal treatment.
N-methylmorpholine (NMM) is used in lubricant formulations for stability and performance.
N-methylmorpholine (NMM) is applied in fuel additive blends.

N-methylmorpholine (NMM) is utilized in laboratory synthesis as a base in organic reactions.
N-methylmorpholine (NMM) is used in acylation and esterification reactions.
N-methylmorpholine (NMM) is applied in halogenation and substitution reactions.

N-methylmorpholine (NMM) is incorporated into pigment and dye production.
N-methylmorpholine (NMM) is used in specialty coatings for enhanced adhesion.
N-methylmorpholine (NMM) is applied in ink formulations requiring stability.

N-methylmorpholine (NMM) is used in fine chemicals as a versatile building block.
N-methylmorpholine (NMM) is an excellent solvent, emulsifier, corrosion inhibitor, Catalyst in polyurethane foamsextraction solvent, stabilizing agent for chlorinated hydrocarbons, and also can be used as pesticide intermediates. 

N-methylmorpholine (NMM) is widely used in the synthesis of pesticide compounds such as insecticide, fungicide, plant growth regulator, etc. 
It is also used in the synthesis of fine chemicals such as surfactant, lubricant coolant, metal antirust agent, fiber treatment agent, etc.
N-methylmorpholine (NMM) is widely used as a catalyst in polyurethane foam production.

N-methylmorpholine (NMM) is employed in the manufacture of rigid, semi-rigid, and flexible polyurethane foams.
N-methylmorpholine (NMM) is applied in polyurethane elastomers and coatings as a reactive catalyst.
N-methylmorpholine (NMM) is utilized as a solvent in organic synthesis.

N-methylmorpholine (NMM) is used to dissolve a wide range of organic compounds.
N-methylmorpholine (NMM) is applied in reaction media requiring polar, aprotic solvents.
N-methylmorpholine (NMM) is incorporated into pharmaceutical synthesis as an intermediate.

N-methylmorpholine (NMM) is used in the preparation of active pharmaceutical ingredients (APIs).
N-methylmorpholine (NMM) is applied as a reagent in peptide synthesis.
N-methylmorpholine (NMM) is used in agrochemical production as a chemical intermediate.

N-methylmorpholine (NMM) is incorporated into herbicide and pesticide formulations.
N-methylmorpholine (NMM) is applied in the synthesis of plant protection agents.
N-methylmorpholine (NMM) is also widely employed as a solvent, reaction medium, or neutralizing agent in various chemical manufacturing and research processes, where its excellent solubility in organic solvents and partial solubility in water allow for uniform dispersion of reagents, stabilization of reactive intermediates, and controlled chemical transformations, thereby improving reaction efficiency, reproducibility, and scalability in industrial and laboratory settings.

Health Hazard:
May cause toxic effects if inhaled or ingested/swallowed. 
Contact with substance may cause severe burns to skin and eyes. 

Fire will produce irritating, corrosive and/or toxic gases. 
Vapors may cause dizziness or suffocation. 
Runoff from fire control or dilution water may cause pollution.

Fire Hazard:
Flammable/combustible material may be ignited by heat, sparks or flames. 
Vapors may form explosive mixtures with air. 
Vapors may travel to source of ignition and flash back. 

Most vapors are heavier than air. 
They will spread along ground and collect in low or confined areas (sewers, basements, tanks). 

Vapor explosion hazard indoors, outdoors or in sewers.
Runoff to sewer may create fire or explosion hazard. 
Containers may explode when heated many liquids are lighter than water.

Safety Profile:
N-methylmorpholine (NMM) is considered a moderately toxic organic amine, and exposure through inhalation of vapors, ingestion, or direct skin contact can cause systemic toxicity, including nausea, headache, dizziness, or central nervous system depression, particularly at high concentrations or prolonged exposure, highlighting the importance of strict occupational hygiene, proper ventilation, and personal protective equipment in industrial and laboratory environments.

Direct contact with N-methylmorpholine (NMM) can result in mild to severe skin irritation, redness, itching, or chemical burns, while accidental contact with the eyes may cause irritation, tearing, pain, or temporary visual discomfort, which necessitates the use of protective gloves, goggles, face shields, and long-sleeved clothing when handling the chemical.
Inhalation of N-methylmorpholine (NMM) vapors or aerosols can lead to respiratory tract irritation, coughing, shortness of breath, sore throat, or exacerbation of pre-existing respiratory conditions, and chronic or repeated inhalation exposure may increase the risk of long-term respiratory effects, underscoring the need for adequate fume hoods, local exhaust ventilation, and respiratory protection during handling.