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N-ethylmorpholine is a colorless liquid with an ammonia-like odor.
N-ethylmorpholine appears as a colorless liquid with a strong ammonia-like odor.
N-ethylmorpholine is miscible with water and many organic solvents, which allows it to participate in a wide range of industrial and laboratory applications.
CAS Number: 100-74-3
Molecular Formula: C6H13NO
Molecular Weight: 115.17
EINECS Number: 202-885-0
Synonyms:4-Ethylmorpholine, N-Ethylmorpholine, 100-74-3, Morpholine 4-ethyl-, Ethylmorpholine, N-Ethylmorfolin, ECM0G991FQ, DTXSID5025312, NSC-6110, DTXCID205312, 202-885-0, N-ethyl morpholine, NSC 6110, 4-ethyl-morpholine, MFCD00006177, N-Ethylmorfolin [Czech], N-ethyl-morpholine, CCRIS 4818, HSDB 1644, EINECS 202-885-0, UNII-ECM0G991FQ, BRN 0102969, AI3-24288, N-ethylmopholine, N-ethyhnorpholine, Texacat NEM, Toyocat NEM, 4-ethylmorpholirie, Dabco NEM, morpholine N-ethyl-, 4-Ethylmorpholine 97%, SCHEMBL3167, SCHEMBL4754, SCHEMBL82948, WLN: T6N DOTJ A2, 4-27-00-00023 (Beilstein Handbook Reference), SCHEMBL153817, SCHEMBL153818, SCHEMBL474212, SCHEMBL7290045, SCHEMBL7290049, SCHEMBL8135220, CHEMBL3561880, N-Ethylmorpholine [HSDB], NSC6110, Tox21_201103, SBB060634, AKOS015901076, 4-Ethylmorpholine ≥97.0% (GC), NCGC00248922-01, NCGC00258655-01, CAS-100-74-3, LS-13196, E0145, NS00019859, ST51046780, F86367, Q2676918, InChI=1/C6H13NO/c1-2-7-3-5-8-6-4-7/h2-6H2,1H, 4-Ethylmorpholine BioXtra suitable for protein sequencing ≥99.5% (GC), 4-ethyl-morpholin, Texacat NEM, Toyocat -NEM, N-ETHYLMORPHOLINE, LUPRAGEN(R) N 104, 4-ETHYLMORPHOLINE, 4-ETHYLMORPHOLINE, FOR PROTEIN SEQUENCE ANALYSIS, N-ETHYLMORPHOLINE 99%
N-ethylmorpholine, also known as 4-Ethylmorpholine or simply Ethylmorpholine, is an organic heterocyclic compound that belongs to the family of morpholine derivatives, which are six-membered rings containing both nitrogen and oxygen atoms.
Severely irritates skin, eyes, and mucous membranes, moderately soluble in water and less dense than water.
N-ethylmorpholine can react vigorously with oxidizing materials.
In this molecule, the nitrogen atom of the morpholine ring is substituted with an ethyl group, which modifies its chemical reactivity, solubility, and industrial usefulness compared to unsubstituted morpholine.
N-ethylmorpholine has the molecular formula C₆H₁₃NO, and it typically appears as a clear, colorless to slightly yellow liquid with an amine-like odor that can be irritating to the nose and throat.
Chemically, N-Ethylmorpholine behaves as a weak base because of the lone electron pair on the nitrogen atom, making it reactive in acid–base chemistry and suitable for use as a catalyst or intermediate in organic synthesis.
N-ethylmorpholine dissolves LiAlH4.
Because of its amphiphilic nature, combining both hydrophilic (oxygen and nitrogen groups) and lipophilic (ethyl group and hydrocarbon ring) properties, it serves as an effective stabilizer, emulsifier, and auxiliary chemical in several chemical processes.
From a structural perspective, N-Ethylmorpholine is valued for its versatility, as the morpholine ring provides chemical stability and resistance to degradation, while the ethyl substitution gives it distinct solubility and reactivity characteristics.
N-ethylmorpholine is manufactured and sold in high purity grades, often above 97–99.5%, depending on whether it is used for industrial production, chemical research, or specialized laboratory techniques such as protein sequencing.
In addition to its basic chemical properties, N-Ethylmorpholine is considered an important intermediate in the synthesis of numerous pharmaceuticals, agrochemicals, and specialty chemicals, because the nitrogen-containing morpholine ring can be functionalized in a variety of ways.
Its ability to act as a tertiary amine allows it to participate in condensation, alkylation, and acylation reactions, making it a valuable building block in organic synthesis for creating more complex molecules.
Moreover, N-Ethylmorpholine is often used as a catalyst or accelerator in industrial processes such as polyurethane production, epoxy resin curing, and polymerization reactions.
Its tertiary amine structure helps promote the cross-linking of polymer chains, enhancing the mechanical properties and durability of the resulting materials.
In this role, even small amounts of N-Ethylmorpholine can significantly influence reaction rates and product quality, which is why it is widely adopted in coatings, adhesives, and sealants manufacturing.
Melting point: –63 °C (lit.),
Boiling point: 139 °C (lit.),
Density: 0.91 g/mL at 20 °C (lit.),
Vapor pressure: 8.1 hPa (20 °C),
Refractive index: n²⁰/D 1.441 (lit.),
Flash point: 82 °F,
Storage temp.: Store below +30 °C,
Solubility: Miscible,
Form: Powder,
pKa: 7.67 (at 25 ℃),
Color: Cream to beige to brown-grey,
pH: 11.8 (100 g/L, H₂O, 20 ℃),
Explosive limit: 1.9% (V),
Viscosity: 1.176 mm²/s,
Water solubility: Miscible,
Freezing point: –63 ℃,
Sensitive: Air sensitive,
BRN: 102969,
Exposure limits: NIOSH REL: TWA 5 ppm (23 mg/m³), IDLH 100 ppm; OSHA PEL: TWA 20 ppm (94 mg/m³); ACGIH TLV: TWA 5 ppm (adopted),
Stability: Stable, flammable, incompatible with strong oxidizing agents, slightly air sensitive,
LogP: 0.08 at 24.6 ℃.
N-Ethylmorpholine is also valued in the chemical industry for its role in corrosion inhibition and metal treatment processes.
Its nitrogen and oxygen atoms can coordinate with metal surfaces, forming protective layers that reduce oxidation and degradation in metals exposed to aqueous or industrial environments.
This makes it particularly useful in cooling systems, metalworking fluids, and certain electrochemical applications, where preventing corrosion is critical for maintaining equipment longevity and operational safety.
In addition, N-Ethylmorpholine can act as a buffering agent in specialized chemical reactions and formulations.
Because it is a weak base, it can moderate pH changes during sensitive reactions, ensuring that the process remains within an optimal chemical window.
This property is especially useful in the synthesis of pharmaceuticals, where reaction conditions must be tightly controlled to avoid byproduct formation or decomposition of active compounds.
From a laboratory perspective, N-Ethylmorpholine’s high purity grades (≥99.5%) make it suitable for biochemical and analytical applications, including protein sequencing, peptide synthesis, and other procedures requiring organic bases that do not introduce contaminants or interfere with sensitive detection methods.
Its miscibility with a wide range of solvents allows it to act as a medium for reactions that involve both polar and nonpolar components.
N-ethylmorpholine is also utilized as a solvent and stabilizer in chemical formulations. Because it is miscible with both water and organic solvents, it can stabilize reactive intermediates, prevent unwanted side reactions, and maintain uniformity in complex mixtures.
This makes it suitable for laboratory applications where precise chemical control is required, such as in analytical chemistry, chromatographic studies, and protein sequencing experiments.
In certain cases, N-Ethylmorpholine functions as a neutralizing agent to adjust pH in formulations that are sensitive to acidic conditions.
Its weakly basic character allows it to safely raise the pH without introducing harsh chemicals that could interfere with the stability or reactivity of other components.
N-Ethylmorpholine’s combination of chemical stability, reactivity, and solubility makes it a versatile compound with broad applications across pharmaceuticals, polymers, coatings, adhesives, and chemical research, while also serving as a reliable intermediate in more complex synthetic pathways.
N-ethylmorpholines use as an intermediate for chemical modification cannot be overstated.
The tertiary amine structure allows for the introduction of functional groups or the construction of more complex heterocyclic compounds, which are foundational in the manufacture of specialty chemicals, pharmaceuticals, and agrochemicals.
Because of this, N-Ethylmorpholine is often regarded as a versatile building block, essential in the design and synthesis of new chemical entities with tailored properties for industrial, research, and medicinal purposes.
Uses:
N-ethylmorpholine’s uses span industrial polymer production, solvent applications, pH adjustment, chemical synthesis, and biochemical research, highlighting its versatility and importance in both commercial and laboratory settings.
N-ethylmorpholine is a component of the buffer used in basic peptide separation through anion-exchange chromatography.
N-ethylmorpholine acts as a catalyst in the preparation of polyurethane foam.
Intermediate for dyestuffs, pharmaceuticals; rubber accelerators and emulsifying agents; solvent for dyes, resins, oils; catalyst in making polyurethane foams.
N-Ethylmorpholine is widely used in industrial, laboratory, and chemical synthesis applications due to its versatile chemical properties as a tertiary amine and heterocyclic compound.
One of its primary uses is as a catalyst or accelerator in polymer chemistry, particularly in the production of polyurethane foams and epoxy resins, where it facilitates cross-linking reactions, increases reaction rates, and improves the mechanical strength and durability of the resulting polymers.
Its presence in small quantities can significantly influence the efficiency of these reactions, making it indispensable in the manufacture of coatings, adhesives, sealants, and elastomers that require precise curing and structural integrity.
In addition to its role in polymerization, N-Ethylmorpholine is frequently used as a solvent or co-solvent in both organic and aqueous systems because of its miscibility with a wide range of polar and nonpolar solvents.
This property allows it to stabilize reactive intermediates, maintain homogeneous reaction mixtures, and facilitate chemical transformations that would otherwise be inefficient or incomplete in less compatible media.
N-ethylmorpholines solvency is also exploited in chemical research laboratories for chromatography, extraction processes, and other analytical techniques requiring a stable, inert medium.
N-ethylmorpholine is also employed as a neutralizing or pH-adjusting agent in various chemical formulations, including industrial cleaning agents, metalworking fluids, and pharmaceutical preparations.
Its weakly basic nature allows it to moderate acidity without introducing strong alkaline conditions that might damage sensitive components or interfere with reaction pathways, making it particularly valuable in delicate chemical processes.
Moreover, N-Ethylmorpholine serves as an intermediate in organic synthesis, where it is used to construct more complex chemical compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
Its morpholine ring provides structural stability and resistance to degradation, while the N-ethyl substitution offers opportunities for further functionalization, allowing chemists to design molecules with tailored properties.
Finally, N-Ethylmorpholine has specialized applications in biochemical and analytical contexts, such as protein sequencing, peptide synthesis, and other laboratory procedures requiring high-purity organic bases that do not introduce contaminants.
In these cases, its combination of chemical stability, solubility, and minimal interference with biological reactions makes it an essential reagent for research and analytical chemistry.
N-Ethylmorpholine is also employed as a corrosion inhibitor and metal treatment agent in industrial applications.
Its nitrogen and oxygen atoms can coordinate with metal surfaces, forming protective layers that prevent oxidation, rust formation, and surface degradation, which is especially valuable in cooling systems, boiler water treatments, and metalworking fluids.
By inhibiting corrosion, it extends the lifespan of equipment, reduces maintenance costs, and improves the overall safety and reliability of industrial operations.
In addition, N-Ethylmorpholine is often utilized in electrochemical and catalytic processes, where its tertiary amine structure allows it to act as a stabilizer or mediator for reactive intermediates.
This property is particularly important in fine chemical synthesis, where precise control over reaction pathways is required to produce high-purity products with minimal byproducts.
N-ethylmorpholines amphiphilic nature, combining hydrophilic and lipophilic properties, also makes it useful in emulsification and formulation of complex chemical mixtures.
Another significant use is as an intermediate in pharmaceutical and agrochemical synthesis, where N-Ethylmorpholine serves as a building block for producing heterocyclic compounds, active pharmaceutical ingredients, and crop protection chemicals.
Its chemical structure allows for functionalization at the nitrogen atom or on the morpholine ring, enabling the creation of derivatives with specific biological activity or chemical functionality.
Safety Profile:
N-ethylmorpholine askin and severe eye irritant.
A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidzing materials.
To fight fire, use alcohol foam, foam, CO2, dry chemical when heated to decomposition it emits toxic fumes of NOx.
Exposure can cause irritation of eyes, nose and throat contact with eyes may result in foggy vision and seeing halos around lights.
Primary irritant (without allergic reaction).
This material is used as a catalyst in polyurethane foam production.
N-ethylmorpholine is a solvent for dyes and resins.
It is used as an intermediate in surfactant, dye, pharmaceutical, and rubber chemical manufacture
N-Ethylmorpholine, while a useful and versatile chemical, poses several hazards that must be carefully managed in both industrial and laboratory settings.
One of the primary concerns is its irritant effect on the respiratory system, skin, and eyes.
Exposure to vapors or aerosols can cause coughing, shortness of breath, and irritation of the mucous membranes in the nose and throat, while direct skin contact may lead to redness, itching, or dermatitis.
Eye exposure can result in severe irritation, tearing, and temporary visual discomfort, making protective gloves, goggles, and adequate ventilation essential during handling.
Another significant hazard is its toxicity upon ingestion or prolonged exposure.
If swallowed, N-Ethylmorpholine can cause nausea, vomiting, abdominal pain, and more severe systemic effects such as central nervous system depression, which may manifest as dizziness, headache, or even confusion in extreme cases.
Repeated or chronic exposure may affect liver and kidney function due to the metabolic processing of the amine, although comprehensive long-term studies are limited.
N-Ethylmorpholine is also flammable, with a relatively low flash point, meaning that it can ignite if exposed to open flames, sparks, or high temperatures.
This creates a risk in industrial environments where heating, mixing, or solvent evaporation occurs, necessitating strict adherence to fire safety protocols, proper storage in flame-resistant containers, and the avoidance of ignition sources.
