Quick Search
4,4′-Methylenedimorpholine is a heterocyclic organic compound consisting of two morpholine rings connected through a central methylene bridge, typically appearing as a clear to pale yellow liquid with a faint amine-like odor and good solubility in water and polar solvents.
4,4′-Methylenedimorpholine functions primarily as a corrosion inhibitor, emulsifier, stabilizer, and biocide, with effectiveness against both gram-positive and gram-negative bacteria, yeast, and fungi, making it useful in water treatment, metalworking fluids, and industrial cleaning products.
Valued for 4,4′-Methylenedimorpholine's multifunctional performance, compatibility with surfactants and detergents, and film-forming anti-rust properties, 4,4′-Methylenedimorpholine is an important additive in protecting materials, extending formulation stability, and supporting diverse industrial applications.
CAS Number: 5625-90-1
EC Number: 227-062-3
Molecular Formula: C9H18N2O2
Molecular Weight: 186.25 g/mol
Synonyms: N,N-Dimorpholinomethane, Morpholine,4,4-methylenebis-, Bis(4-morpholinyl)methane, N,N'-Methylenebismorpholine, 4,4'-methanediyldimorpholine, 4,4-methylenebis-Morpholine, N,N-Methylene-bis-morpholine, N,N'-Dimorpholinomethane, 4-(Morpholin-4-ylMethyl)Morpholine, Conncide MW, SIDCHEM LB 69, DIMORPHOLINOMETHONE, DIMORPHOLINOMETHANE, bismorpholinomethane, bis(morpholino-)methan, MORPHOLINE44METHYLENEDI, BIS-(MORPHOLINE-)METHANE, 44METHYLENEBISMORPHOLINE, N,N'-DIMORPHOLINOMETHANE, 4,4'-methylenedi-morpholin, 4,4'-methylenedimorpholine, bis(morpholino-)methan, bismorpholinomethane, N,N'-Methylenebismorpholine, DIMORPHOLINOMETHANE, DIMORPHOLINOMETHONE, N,N-Dimorpholinomethane, Morpholine, 4,4′-methylenebis-, Bis(4-morpholinyl)methane, N,N′-Methylenebismorpholine, 4,4′-methanediyldimorpholine, 4,4-methylenebis-Morpholine, DIMORPHOLINOMETHANE, DIMORPHOLINOMETHONE, bismorpholinomethane, bis(morpholino-)methane, N,N'-DIMORPHOLINOMETHANE, 4,4’-methylenedi-morpholin, 4,4’-methylenedimorpholine, N,N'-Dimorpholinomethane, N,N´-Methylene bismorpholine, Bis (morpholino-) methan, Bismorpholino methane, 4,4-Methylenedimorpholine, Morpholine, 4,4-methylenedi-, N,N'-Methylene-bis-morpholine, Methylenebistetrahydro-1,4-oxazine, Methylenebisoxazine, Dimorpholinomethan, Bismorpholinomethan
4,4′-Methylenedimorpholine is an organic heterocyclic compound formed by linking two morpholine rings through a methylene bridge.
4,4′-Methylenedimorpholine appears as a clear to pale yellow liquid with a faint amine-like odor and is soluble in water and many polar organic solvents.
4,4′-Methylenedimorpholine functions primarily as a corrosion inhibitor, emulsifier, and chemical intermediate, finding application in water treatment formulations, lubricants, and industrial cleaning products.
4,4′-Methylenedimorpholine's morpholine-based structure provides both hydrophilic and hydrophobic characteristics, allowing it to act as a stabilizer in emulsions and a protective agent against metal corrosion in aqueous systems.
4,4′-Methylenedimorpholine is valued in industrial chemistry for its compatibility with surfactants, detergents, and other additives, as well as for its role in enhancing formulation stability.
4,4′-Methylenedimorpholine is a low toxicity and water-based biocide developed for use in metal working concentrates.
4,4′-Methylenedimorpholine is effective against a wide range of microorganisms including gram positive and gram negative bacteria, yeast and fungi.
Microorganisms grow at a rapid rate and without use of the correct biocide, numbers can increase dramatically.
4,4′-Methylenedimorpholine is a chemical compound from the group of nitrogen - oxygen heterocycles.
4,4′-Methylenedimorpholine, with the CAS number 5625-90-1, is an organic compound characterized by its morpholine functional groups.
4,4′-Methylenedimorpholine typically appears as a colorless to pale yellow liquid or solid, depending on the temperature and purity.
4,4′-Methylenedimorpholine has a relatively low toxicity profile, but like many chemical substances, it should be handled with care to avoid skin and eye irritation.
4,4′-Methylenedimorpholine's reactivity is primarily attributed to the presence of the morpholine rings, which can participate in various chemical reactions, including cross-linking processes in polymer chemistry.
Overall, 4,4′-Methylenedimorpholine is valued for its functional properties in the production of durable and resilient materials.
Sexual fungicide, 4,4′-Methylenedimorpholine has good solubility, suitable for oil and water based systems.
In addition to the bactericidal effect, 4,4′-Methylenedimorpholine also has a certain anti-rust effect of black metal.
4,4′-Methylenedimorpholine is a new generation of broad spectrum and low toxicity developed for water-based metalworking fluids
Sexual fungicide, 4,4′-Methylenedimorpholine has good solubility, suitable for oil and water based systems.
In addition to the bactericidal effect, 4,4′-Methylenedimorpholine also has a certain anti-rust effect of black metal.
4,4′-Methylenedimorpholine is effective against both gram-negative and Gram-positive bacteria.
4,4′-Methylenedimorpholine is a heterocyclic organic compound consisting of two morpholine rings connected through a central methylene bridge, giving it a unique bifunctional amine oxide structure that combines both polar and non-polar characteristics.
Typically appearing as a clear to pale yellow liquid with a faint amine-like odor, 4,4′-Methylenedimorpholine is miscible with water and polar solvents, while also showing compatibility with a wide range of organic solvents and surfactants.
Industrially, 4,4′-Methylenedimorpholine is used as a corrosion inhibitor in cooling water systems, boiler treatments, and metalworking fluids, where its ability to form protective films helps prevent oxidative and chemical degradation of metal surfaces.
In addition, 4,4′-Methylenedimorpholine functions as an emulsifier, stabilizer, and co-surfactant in various formulations, improving solubility, dispersion, and overall stability in cleaning agents, lubricants, and coatings.
4,4′-Methylenedimorpholine's morpholine-derived structure contributes to strong film-forming and buffering properties, allowing it to stabilize formulations under a wide pH range and extend the service life of treated systems.
Beyond water treatment and industrial cleaning, 4,4′-Methylenedimorpholine is also employed as a chemical intermediate, serving as a building block in the synthesis of specialty chemicals and polymers.
Due to 4,4′-Methylenedimorpholine's reactivity and potential to release morpholine under harsh conditions, careful handling, storage, and formulation control are essential to maintain product quality and ensure worker safety.
Overall, 4,4′-Methylenedimorpholine is valued for its multifunctional performance, versatility in formulation chemistry, and protective effects, making it an important additive in diverse industrial applications.
Market Overview of 4,4′-Methylenedimorpholine:
The market for 4,4′-Methylenedimorpholine is niche but steadily expanding, driven by its dual functionality as both a corrosion inhibitor and industrial biocide.
4,4′-Methylenedimorpholine is primarily used in water treatment systems, metalworking fluids, lubricants, and natural rubber latex preservation, where it helps protect equipment and materials from microbial degradation and chemical corrosion.
4,4′-Methylenedimorpholine belongs to the broader morpholine derivatives market, which is valued at over USD 3.5 billion and growing at around 5–7% CAGR, and it also overlaps with the global corrosion inhibitors sector, estimated at nearly USD 9 billion in 2024 with steady growth projections.
Demand is particularly strong in industrializing regions across Asia-Pacific and the Middle East, where manufacturing, automotive, and oilfield industries rely heavily on protective additives.
Key growth drivers include the push for multifunctional, cost-efficient additives, increasing industrial output, and the need to extend the service life of fluids and equipment.
However, challenges such as regulatory scrutiny of biocides, competition from established inhibitors, and cost sensitivity may limit rapid adoption.
Overall, 4,4′-Methylenedimorpholine is expected to gain wider use as industries seek versatile, effective, and formulation-friendly solutions for corrosion protection and microbial control.
Uses of 4,4′-Methylenedimorpholine:
4,4′-Methylenedimorpholine is known for its role as a hardener or curing agent in epoxy resins and is often utilized in various industrial applications due to its ability to enhance the mechanical properties of materials.
4,4′-Methylenedimorpholine exhibits good solubility in water and organic solvents, making it versatile for different formulations.
4,4′-Methylenedimorpholine serves as a broad-spectrum biocide/preservative, particularly in water-based metalworking fluids (MWF)—protecting against bacteria and fungi.
Typical in-can usage of 4,4′-Methylenedimorpholine: ~0.15% w/w in MWF; recommended addition: 2–3% in concentrate, 0.1–0.2% (1–2 ‰) in working liquid.
4,4′-Methylenedimorpholine offers advantages such as low toxicity, mild odor, low irritation, and good formulation compatibility and stability in fluids
4,4′-Methylenedimorpholine was previously approved for use as a biocide in the EEA and/or Switzerland, and this approval has now expired, for: product preservation, preservation for working / cutting fluids.
Metal cutting fluid bactericide 4,4′-Methylenedimorpholine is a slow-release bactericide with a broad spectrum and high efficiency and a certain gas-phase sterilization ability.
4,4′-Methylenedimorpholine is suitable for inhibiting the growth and reproduction of microorganisms in various humid environments, preventing the generation of putrefaction and foul odors, and ensuring safe operation of the system.
4,4′-Methylenedimorpholine is employed as intermediate for pharmaceutical.
4,4′-Methylenedimorpholine is used as a curing agent in epoxy resins and as a stabilizer in industrial chemical formulations.
4,4′-Methylenedimorpholine enhances the properties and longevity of cured materials.
4,4′-Methylenedimorpholine is a highly effective biocide specifically developed for metalworking fluids (MWFs), such as cutting oils, coolants, and lubricants.
4,4′-Methylenedimorpholine is renowned for its broad-spectrum antimicrobial properties, making it an ideal solution for the control of bacteria, fungi, and algae that can cause contamination in industrial fluids.
As a mildly toxic and environmentally friendly agent, 4,4′-Methylenedimorpholine is a key choice for industries where safety and sustainability are paramount.
4,4′-Methylenedimorpholine is a formaldehyde-releasing preservative and is used as a component of metalworking fluids.
4,4′-Methylenedimorpholine is a useful reagent for electron-rich heterocycles (pyrroles, indoles) and active methylene compounds in the presence of trifluoroacetic acid.
Strong Compatibility:
4,4′-Methylenedimorpholine is highly compatible with a variety of metalworking fluid formulations, including concentrates and ready-to-use solutions.
This flexibility makes 4,4′-Methylenedimorpholine suitable for diverse applications in industries like automotive, aerospace, and precision machining.
Oilfield Desulfurization uses:
4,4′-Methylenedimorpholine is an effective biocide used in oilfield desulfurization processes to control microbial growth.
Sulfur compounds in oilfields often promote the growth of microbes, leading to corrosion and quality degradation of the extracted oil.
4,4′-Methylenedimorpholine’s broad-spectrum antimicrobial action helps prevent the proliferation of bacteria, fungi, and other microbes in the oil, reducing the impact of sulfur compounds and improving the overall efficiency of the desulfurization process.
This ensures the smooth operation of oilfield equipment and enhances the quality of extracted oil.
Water Treatment uses:
4,4′-Methylenedimorpholine is widely used in water treatment systems, including industrial wastewater, circulating water systems, and municipal wastewater treatment.
In these processes, 4,4′-Methylenedimorpholine acts as a powerful biocide to control the growth of bacteria, fungi, and algae.
4,4′-Methylenedimorpholine's broad-spectrum antimicrobial properties help prevent biofouling, ensuring water quality and reducing maintenance costs.
The use of 4,4′-Methylenedimorpholine also contributes to the efficiency of water treatment processes by keeping microbial contamination at bay and preventing the corrosion of system components.
Metalworking Fluids uses:
In metalworking, 4,4′-Methylenedimorpholine is commonly used in metalworking fluids (MWFs), such as cutting fluids and coolants, to prevent microbial growth.
Metalworking fluids are highly susceptible to microbial contamination due to their aqueous nature and the presence of organic matter.
4,4′-Methylenedimorpholine effectively inhibits the growth of bacteria, fungi, and yeasts in these fluids, preventing foul odors, sludge formation, and corrosion.
This not only extends the service life of the metalworking fluid but also ensures a cleaner and more efficient machining process.
Coatings uses:
In the coatings and paints industry, 4,4′-Methylenedimorpholine is used as an antimicrobial and anti-fungal agent.
4,4′-Methylenedimorpholine helps prevent the growth of mold and bacteria in paints, ensuring the quality of the product during storage and application.
In environments with high humidity or moisture, 4,4′-Methylenedimorpholine enhances the durability and performance of coatings by protecting them from microbial degradation.
This makes 4,4′-Methylenedimorpholine particularly useful for coatings used in damp or humid conditions, such as those applied in marine or industrial environments.
Lubricants uses:
4,4′-Methylenedimorpholine is also used in lubricants to prevent microbial contamination.
In lubricating oils, the growth of bacteria and fungi can lead to system failures and corrosion of mechanical parts.
4,4′-Methylenedimorpholine’s biocidal properties help ensure that lubricants remain free from microbial growth, extending the life of the lubricant and the machinery it protects.
This is especially important for industrial machinery and automotive systems where the performance and stability of lubricants are critical.
Leather Anti-fungal Protection uses:
In the leather industry, 4,4′-Methylenedimorpholine is used to prevent fungal and bacterial contamination in leather products, especially in humid and wet environments.
Leather, being organic, is highly prone to microbial growth, which can lead to deterioration, unpleasant odors, and discoloration.
By applying 4,4′-Methylenedimorpholine, manufacturers can protect leather goods, such as shoes, bags, and furniture, from microbial damage, thereby extending their lifespan and preserving their quality.
Pulp and Paper Industry uses:
In the pulp and paper industry, 4,4′-Methylenedimorpholine is used to inhibit microbial growth in the pulp slurry.
In this industry, the moist conditions are ideal for the proliferation of bacteria and fungi, which can lead to the spoilage of pulp, paper, and equipment.
4,4′-Methylenedimorpholine’s antimicrobial properties ensure that the pulp remains free from microbial contamination, helping improve the quality of the final paper product and prolonging the life of production equipment.
4,4′-Methylenedimorpholine is especially useful in preventing mold and mildew, which can affect the quality of paper and cause production delays.
Adhesives uses:
In adhesive formulations, 4,4′-Methylenedimorpholine serves as a biocide to prevent microbial contamination.
Adhesives are often used in environments where moisture is present, making them susceptible to microbial growth.
4,4′-Methylenedimorpholine helps protect adhesives from mold and bacteria, ensuring that they maintain their effectiveness and stability over time.
This is particularly important in applications such as packaging, construction, and automotive industries, where the quality and durability of adhesives are paramount.
Organic synthesis uses:
4,4′-Methylenedimorpholine, as an important intermediate raw material, plays a key role in organic synthesis reactions.
4,4′-Methylenedimorpholine can participate in a variety of chemical reactions to generate compounds with specific structures and functions.
Oil additives uses:
4,4′-Methylenedimorpholine has excellent oil solubility and solubility balance, making it ideal for oil additives.
4,4′-Methylenedimorpholine improves oil stability and performance and extends oil life.
Biocide uses:
4,4′-Methylenedimorpholine is a broad-spectrum bactericide that inhibits and kills microorganisms such as bacteria, fungi and yeasts.
4,4′-Methylenedimorpholine can be used in emulsions, semi-synthetic and fully synthetic metalworking fluids, coatings, paper, adhesives, etc.
4,4′-Methylenedimorpholine prevents the growth of moulds and bacteria in humid environments.
Production of 4,4′-Methylenedimorpholine:
4,4′-Methylenedimorpholine is typically synthesized through a condensation reaction involving morpholine and formaldehyde under controlled conditions.
In the process, two morpholine molecules react with a methylene donor (commonly formaldehyde or paraformaldehyde) to form the methylene bridge that links the two morpholine rings.
The reaction is usually carried out in aqueous or alcoholic medium with controlled pH, as both acidic and basic conditions can influence selectivity and yield.
Catalysts or stabilizers may be employed to minimize by-products, such as polymeric formaldehyde derivatives or partially substituted morpholines.
The crude product is then subjected to neutralization, purification, and distillation or crystallization to obtain a high-purity 4,4′-Methylenedimorpholine suitable for industrial applications.
The final compound generally appears as a clear to pale yellow liquid with amine-like odor, fully miscible with water and many polar solvents, making it easy to integrate into formulations.
Industrial production is conducted under Good Manufacturing Practice (GMP) or equivalent standards, particularly when 4,4′-Methylenedimorpholine is intended for use in sensitive industries such as water treatment, lubricants, and latex preservation.
Stringent quality control testing is required to verify identity, purity, stability, and performance characteristics, ensuring that the material consistently meets specifications for use as a corrosion inhibitor, emulsifier, or preservative.
History of 4,4′-Methylenedimorpholine:
4,4′-Methylenedimorpholine emerged in the mid-to-late 20th century as part of broader industrial research into morpholine derivatives, which were already valued for their roles as solvents, corrosion inhibitors, and intermediates in rubber and textile chemistry.
Morpholine itself had been used since the early 1900s, but the introduction of methylene-bridged structures such as 4,4′-Methylenedimorpholine offered enhanced stability and multifunctional properties.
Early patents and industrial literature from the 1960s and 1970s describe 4,4′-Methylenedimorpholine as a dual-function additive combining corrosion inhibition with biocidal activity, making it particularly useful in cooling water systems, metalworking fluids, and boiler treatments at a time when industrial infrastructure was rapidly expanding worldwide.
Over the following decades, 4,4′-Methylenedimorpholine found specialized applications in the rubber and latex industry, where it was shown to help preserve natural rubber latex during storage and transportation, reducing microbial spoilage and odor formation.
4,4′-Methylenedimorpholine's use expanded into lubricants, coatings, and industrial cleaning formulations, aligning with the trend toward multifunctional additives that could simplify formulations while delivering strong protective performance.
In recent years, 4,4′-Methylenedimorpholine has drawn attention as a cost-effective and versatile chemical, especially in emerging markets with growing industrial and manufacturing sectors.
While 4,4′-Methylenedimorpholine remains a specialty chemical compared to more widely known inhibitors, its longstanding track record, reliable performance, and adaptability continue to support its relevance in modern industrial chemistry.
Handling and Storage of 4,4′-Methylenedimorpholine:
Handling:
Avoid contact with eyes, skin, and clothing.
Prevent formation of mists/aerosols.
Use only in well-ventilated areas or under local exhaust.
Do not eat, drink, or smoke while handling.
Wear appropriate PPE (chemical-resistant gloves, goggles, lab coat).
Wash hands thoroughly after use and at shift end.
Storage:
Store in tightly closed, properly labeled containers in a cool, dry, well-ventilated place.
Protect from heat, sparks, and direct sunlight.
Keep away from strong oxidizers, strong acids, and acylating agents.
Minimize moisture ingress (close lids promptly; nitrogen blanket if long-term bulk storage).
Stability and Reactivity of 4,4′-Methylenedimorpholine:
Stability:
Stable under normal temperatures and pressures; does not polymerize.
Reactivity:
Amphiphilic amine ether; incompatible with strong oxidizers and strong acids.
Prolonged exposure to moisture may affect quality.
Hazardous Decomposition Products:
Nitrogen oxides (NOx), carbon monoxide (CO), carbon dioxide (CO₂), and irritating vapors under fire/thermal decomposition.
Incompatibilities:
Strong oxidizing agents; strong acids; acid chlorides/anhydrides; powerful acylation/alkylation reagents.
First Aid Measures of 4,4′-Methylenedimorpholine:
Inhalation:
Move to fresh air.
Keep at rest, warm.
If cough, breathing difficulty, or irritation persists, get medical attention.
Skin Contact:
Remove contaminated clothing.
Rinse skin with plenty of water and mild soap for ≥15 minutes.
Seek medical advice if redness/irritation develops.
Eye Contact:
Rinse cautiously with water for ≥15 minutes, lifting upper/lower lids.
Remove contact lenses if easy.
Obtain medical attention if irritation persists.
Ingestion:
Rinse mouth.
Do not induce vomiting.
Give small amounts of water if conscious.
Call a physician/poison center if unwell or large amount ingested.
General:
Show this sheet to the provider.
Wash contaminated clothing before reuse.
Firefighting Measures of 4,4′-Methylenedimorpholine:
Suitable Extinguishing Media:
Water spray/fog, alcohol-resistant foam, dry chemical, or CO₂.
Avoid high-pressure water jets.
Specific Hazards:
Combustible liquid; heating may produce toxic/irritating fumes (NOx, CO).
Containers may rupture if heated.
Protective Equipment for Firefighters:
Self-contained breathing apparatus (SCBA) and full protective gear.
Cool exposed containers with water spray.
Prevent contaminated runoff from entering drains/waterways.
Accidental Release Measures of 4,4′-Methylenedimorpholine:
Personal Precautions:
Evacuate non-essential personnel.
Ensure adequate ventilation.
Avoid skin/eye contact and inhalation of mist.
Remove ignition sources.
Wear gloves, goggles/face shield, protective clothing; use a respirator if airborne concentrations may be significant.
Spill Cleanup:
Dike to contain.
Absorb with inert material (sand, vermiculite, universal absorbent).
Collect into labeled, sealable containers for disposal.
Wash spill area with water and mild detergent; prevent washings from entering drains.
Environmental Precautions:
Avoid release to the environment.
Prevent entry into sewers/surface waters; notify authorities if significant release occurs.
Exposure Controls / Personal Protective Equipment of 4,4′-Methylenedimorpholine:
Engineering Controls:
Use local exhaust ventilation to keep airborne mist/vapor as low as reasonably achievable.
Provide eyewash and safety shower near handling areas.
Respiratory Protection:
Not typically required in well-ventilated settings.
If ventilation is inadequate or aerosols are generated, use a NIOSH-approved organic vapor/particulate respirator per risk assessment.
Hand Protection:
Chemical-resistant gloves (nitrile, neoprene, or butyl rubber).
Inspect/replace regularly.
Eye/Face Protection:
Safety goggles meeting ANSI Z87.1 (or equivalent); add face shield for bulk transfers/splash risk.
Skin/Body Protection:
Lab coat or chemical-resistant coveralls; chemical-resistant apron for large-volume handling.
Hygiene Measures:
Do not eat, drink, or smoke when using this product.
Wash hands/forearms after handling.
Remove PPE carefully to avoid contamination.
Launder contaminated clothing before reuse.
Identifiers of 4,4′-Methylenedimorpholine:
Substance Name: 4,4′-Methylenedimorpholine
IUPAC Name: 4,4'-Methylenebis(morpholine)
CAS Number: 5625-90-1
EC (EINECS) Number: 227-062-3
Molecular Formula: C₉H₁₈N₂O₂
Molecular Weight: 186.25 g/mol
InChI: InChI=1S/C9H18N2O2/c1-10-5-7-13-9(6-11-2)8-12-3-4-11-6/h9H,5-8H2,1-4H3
InChI Key: XQXMKYXHYUKKJW-UHFFFAOYSA-N
SMILES: C1COCCN1CN2CCOCC2
PubChem CID: 12568
ChemSpider ID: 12058
UN Number (Transport): Not classified as a dangerous good under UN regulations
HS Code: Typically falls under 2934 (heterocyclic compounds with nitrogen hetero-atom(s))
Chemical Formula: C9H18N2O2
Molecular Weight: 186.25 g/mol
CAS Number: 5625-90-1
EC Number: 227-062-3
Appearance: Colorless to light yellow liquid; slightly amine-like odor
Density: 1.04 g/cm³
Melting Point: 18–21 °C
Boiling Point: 122–124 °C at 12 mmHg; ~265 °C at 760 mmHg
Flash Point: 77.6 °C
Vapor Pressure: 0.00935 mmHg at 25 °C (~0.625 Pa)
Water Solubility: Soluble in water; fully miscible between 10–30 °C, pH 5–9
pKa: 6.91 ± 0.10 (Predicted)
Refractive Index: 1.4790 (estimated)
Storage Conditions: 2–8 °C
SMILES: C(N1CCOCC1)N1CCOCC1
InChI: InChI=1S/C9H18N2O2/c1-5-12-6-2-10(1)9-11-3-7-13-8-4-11/h1-9H2
InChIKey: MIFZZKZNMWTHJK-UHFFFAOYSA-N
IUPAC Name: 4-(morpholin-4-ylmethyl)morpholine
Substance Name: 4,4′-Methylenedimorpholine
IUPAC Name: 4,4'-Methylenebis(morpholine)
Other Systematic Name: N,N'-Methylenebis(morpholine)
Bis(morpholin-4-yl)methane
CAS Number: 5625-90-1
EC (EINECS) Number: 227-062-3
UNII (FDA Unique Ingredient Identifier): Not assigned
PubChem CID: 12568
ChemSpider ID: 12058
ChEBI ID: CHEBI:88259
KEGG ID: C19691
Molecular Formula: C₉H₁₈N₂O₂
Molecular Weight: 186.25 g/mol
InChI: InChI=1S/C9H18N2O2/c1-10-5-7-13-9(6-11-2)8-12-3-4-11-6/h9H,5-8H2,1-4H3
InChI Key: XQXMKYXHYUKKJW-UHFFFAOYSA-N
SMILES: C1COCCN1CN2CCOCC2
ATC Code: Not assigned (industrial chemical, not pharmaceutical)
HS Code: 2934.99 (heterocyclic compounds with nitrogen hetero-atom(s), not elsewhere specified)
RTECS Number: Not widely reported
Regulatory Status: Specialty industrial chemical; not classified as a dangerous good under UN transport regulations.
Properties of 4,4′-Methylenedimorpholine:
Substance Name: 4,4′-Methylenedimorpholine
Molecular Formula: C₉H₁₈N₂O₂
Molecular Weight: 186.25 g/mol
Physical State: Liquid (can appear as clear to pale yellow, slightly viscous liquid)
Color: Colorless to pale yellow
Odor: Mild amine-like odor
Density: ~1.07–1.10 g/cm³ at 20 °C
Melting Point: Not well defined (remains liquid at ambient conditions)
Boiling Point: ~285–290 °C at 760 mmHg
Flash Point: ~127–130 °C (closed cup)
Molecular Weight: 186.25 g/mol
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Topological Polar Surface Area: 24.9 Ų
Heavy Atom Count: 13
Exact Mass: 186.137 g/mol
Monoisotopic Mass: 186.137 g/mol
XLogP3: -0.3
Complexity: 127
Covalently-Bonded Unit Count: 1
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Compound Is Canonicalized: Yes
Substance Name: 4,4′-Methylenedimorpholine
Molecular Formula: C₉H₁₈N₂O₂
Molecular Weight: 186.25 g/mol
Appearance: Clear to pale yellow, slightly viscous liquid
Odor: Mild, amine-like
Density (20 °C): 1.07–1.10 g/cm³
Melting Point: Not sharply defined; remains liquid at ambient temperature
Boiling Point: ~285–290 °C at 760 mmHg
Flash Point: ~127–130 °C (closed cup)
Autoignition Temperature: ~400 °C (estimated)
Viscosity (20 °C): ~20–25 mPa·s
Refractive Index (n²⁰D): 1.463–1.468
