IMIDAZOLIDONE (2-IMIDAZOLIDONE)
Imidazolidone (2-imidazolidone) is a cyclic urea compound that functions as a versatile intermediate in various chemical reactions.
Imidazolidone (2-imidazolidone) can act as a chelating agent, forming complexes with metal ions and enabling their use in catalytic processes.
Imidazolidone (2-imidazolidone) acts as a bifunctional molecule, capable of participating in both nucleophilic addition and condensation reactions.
CAS Number: 120-93-4
EC Number: 204-436-4
Molecular Formula: C3H6N2O
Molecular Weight: 86.09
Synonyms: ETHYLENEUREA, imidazolidinone, Ethylene urea, 2-Oxoimidazolidine, 1,3-Ethyleneurea, Monoethyleneurea, 2-Oxomidazolidine, SD 6073, Urea, N,N'-(1,2-ethanediyl)-, DTXSID0020602, NSC-21314, DTXCID20602, 2K48456N55, CHEBI:37001, RefChem:596753, CHEBI:55370, 204-436-4, N,N'-Ethyleneurea, Imidazolid-2-one, 2-imidazolidinon, Urea, 1,3-ethylene-, MFCD00005257, NSC 21314, 2-Imidazolidone, 96%, Urea,3-ethylene-, WLN: T5MVMTJ, Urea,N'-(1,2-ethanediyl)-, HSDB 4021, EINECS 204-436-4, imidazolidone, 2-imidazolinone, AI3-22151, imidazolin-2-one, mancozeb TP2, UNII-2K48456N55, Imidazoliden-2-one, 2-oxo-imidazolidine, Clonidine Impurity 6, EC 204-436-4, ETHYLENEUREA [HSDB], SCHEMBL2479, SCHEMBL9827, 2-Imidazolidone - Anhydrous, SCHEMBL16730, CHEMBL12034, SCHEMBL293787, orb1310433, SCHEMBL1599923, SCHEMBL2707176, SCHEMBL2783204, SCHEMBL3376425, SCHEMBL6274768, SCHEMBL8863980, 2-IMIDAZOLIDINONE [MI], NSC3338, BB_SC-12808, NSC-3338, NSC21314, Tox21_200783, EBC-04357, MSK158188, AKOS000121325, FI47232, HY-W031536, NCGC00248832-01, NCGC00258337-01, AS-13128, BP-21148, CAS-120-93-4, PD065555, DB-021217, DB-021218, CS-0075560, I0005, NS00008037, EN300-21266, D71145, 2-Imidazolidinon 100 microg/mL in Acetonitrile, F078654, 2-Imidazolidone, PESTANAL(R), analytical standard, Q2813813, F0001-0335, Z104494954, InChI=1/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6, 65118-65-2
Imidazolidone (2-imidazolidone) is a heterocyclic organic compound characterized by a five-membered ring containing two nitrogen atoms and a carbonyl group.
Imidazolidone (2-imidazolidone) typically appears as a white to off-white crystalline solid and exhibits good chemical stability under normal conditions.
Due to its amide-like structure, Imidazolidone (2-imidazolidone) shows moderate polarity and the ability to form hydrogen bonds, which contributes to its functionality in various chemical systems.
Imidazolidone (2-imidazolidone) serves as a key structural unit in many derivatives used across pharmaceutical, cosmetic, and industrial applications, where it plays roles in formulation stability and chemical synthesis.
Imidazolidone (2-imidazolidone) is a cyclic urea compound that functions as a versatile intermediate in various chemical reactions.
Imidazolidone (2-imidazolidone) acts as a bifunctional molecule, capable of participating in both nucleophilic addition and condensation reactions.
Imidazolidone (2-imidazolidone) mechanism of action involves the formation of stable intermediates through the interaction of its carbonyl group with electrophiles, facilitating the synthesis of diverse organic compounds.
Imidazolidone (2-imidazolidone) can act as a chelating agent, forming complexes with metal ions and enabling their use in catalytic processes.
Imidazolidone (2-imidazolidone)'s functional role lies in its ability to serve as a building block for the synthesis of agrochemicals, and other fine chemicals.
Imidazolidone (2-imidazolidone)'s mechanism of action involves the formation of covalent bonds with other molecules, allowing for the creation of complex molecular structures with potential applications in various development endeavors.
Imidazolidinones are a class of 5-membered ring heterocycles structurally related to imidazolidine.
Imidazolidinones feature a saturated C3N2 nucleus, except for the presence of a urea or amide functional group in the 2 or 4 positions.
Imidazolidone (2-imidazolidone) is cyclic derivatives of urea.
1,3-Dimethyl-2-imidazolidinone is a polar solvent and Lewis base.
Drugs featuring this ring system include emicerfont, imidapril, and azlocillin.
Dimethylol ethylene urea is the reagent used in permanent press clothing.
Imidazolidone (2-imidazolidone) is used as a formaldehyde scavenger in amino-resin systems and textile finishes.
Imidazolidone (2-imidazolidone) is a cyclic urea derivative.
Imidazolidone (2-imidazolidone) is used as an intermediate in organic synthesis and as a building block for substituted imidazolidinones.
Uses of Imidazolidone (2-Imidazolidone):
Imidazolidone (2-imidazolidone) is principally used as a formaldehyde scavenger in amino-resin systems and textile finishes.
Imidazolidone (2-imidazolidone) reacts with free formaldehyde and with pendant N-methylol groups to form stable adducts, lowering free formaldehyde content and emissions.
Imidazolidone (2-imidazolidone) is used as an intermediate in pharmaceutical synthesis, where it serves as a building block for the production of various active compounds.
Imidazolidone (2-imidazolidone) is applied in cosmetic and personal care formulations, particularly through its derivatives, which function as preservatives and antimicrobial agents to extend product shelf life.
Imidazolidone (2-imidazolidone) is also utilized in the production of resins and polymer systems, contributing to material stability and performance.
In addition, Imidazolidone (2-imidazolidone) is employed in textile processing and finishing chemicals, where it helps improve fabric properties and durability.
Imidazolidone (2-imidazolidone) is used for the production of dimethylol ethylene urea thermosetting resins in textiles and paper.
Imidazolidone (2-imidazolidone) is used as a scavenging agent to reduce the free formaldehyde in phenolic, melamine, glyoxal and urea formaldehyde resin systems for the coatings, construction and textile industries.
Imidazolidone (2-imidazolidone) is used to make high polymers, plasticizers, lacquers, adhesives, and textile and leather finishing agents.
Imidazolidone (2-imidazolidone) is also used as an insecticide.
Coating and Paint:
Imidazolidone (2-imidazolidone) can be used as a de-aldehyde agent in poly-EVA, water-based coatings, paints, pigments, adhesives, and the paper industry.
Imidazolidone (2-imidazolidone) can also be added to the paint alone to make the paint absorb and decompose formaldehyde.
Ink for inkjet printers:
Imidazolidone (2-imidazolidone) is an important additives of ink for inkjets.
Imidazolidone (2-imidazolidone) can disperse the pigment, lubricate the channels, prevent nozzles from drying out and blocking, and improve the storage stability of the ink.
Imidazolidone (2-imidazolidone) can also improve the color contrast to enhance the printing effect.
Daily Chemical:
Imidazolidone (2-imidazolidone) is the main component of a household de-aldehyde agent.
Imidazolidone (2-imidazolidone) can be used as a high-performance formaldehyde remover, home air formaldehyde potent enzyme, formaldehyde long-acting melting medium, aldehyde remover for glue, photocatalyst, floor deodorization care wax, furniture deodorizer, car deodorizer, etc.
Organic Synthesis:
Imidazolidone (2-imidazolidone) can be used as intermediates of many new antibiotics, such as meloxicillin and aloxicillin, for anti-schistosomiasis drugs and as basic raw materials of third-generation penicillin.
In the biological field, Imidazolidone (2-imidazolidone) can be used to produce plant growth regulators, fungicides, inhibitors, herbicides, etc., such as N-chlorocarbonyl-2-imidazolidinone, 1-chlorocarbonyl-3-acetyl-2-imidazolidinone, 1-chlorocarbonyl-3-methanesulfonyl-2-imidazolidinone N-chloroformyl-2-imidazolidinone, 1-chloroformyl-3-acetyl-2-imidazolidinone, 1-chloroformyl-3-methanesulfonyl-2-imidazolidinone, N-hydroxyethyl-2-imidazolidinone, 1-methanesulfonyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-acetyl-2-imidazolidinone, etc.
Industry Uses:
Fragrance
Wrinkle resisting agent
Intermediates
Consumer Uses:
Fragrance
Solvent
Wrinkle resisting agent
Applications of Imidazolidone (2-Imidazolidone):
Reactant for synthesis of:
Chiral microporous materials from achiral precursors
Aryl and heteroaryl N-acylureas via microwave-assisted palladium-catalyzed carbonylation
A highly water-soluble peptide based human neutrophil elastase inhibitor
Heterocycles by cyanoacetylation for antimicrobial use
Reactant for:
Pd-catalyzed C-N bond formation with heteroaromatic tosylates
Oxidative amidation of activated alkenes
Preparation of Imidazolidone (2-Imidazolidone):
Imidazolidone (2-imidazolidone) can be obtained by the direct condensation of ethylenediamine with urea or dimethyl carbonate:
C2H4(NH2)2 + CO(NH2)2 → C3H6N2O + 2 NH3
H2N–CH2–CH2–NH2 + (MeO)2CO → C3H6N2O + 2 MeOH
Imidazolidone (2-imidazolidone) can also be obtained by the direct condensation of ethylene glycol and urea:
CO(NH2)2 + HO–CH2–CH2–OH → C3H6N2O + 2 H2O
History of Imidazolidone (2-Imidazolidone):
Imidazolidone (2-imidazolidone) and its derivatives have their origins in early 20th-century developments in heterocyclic chemistry, when researchers began exploring nitrogen-containing ring structures for their reactivity and functional versatility.
As organic chemistry advanced, Imidazolidone (2-imidazolidone) gained importance as a stable cyclic urea compound derived from ethylenediamine and carbonyl sources.
During the mid-20th century, Imidazolidone (2-imidazolidone)'s relevance increased with the growth of the pharmaceutical and polymer industries, where it was used as an intermediate for synthesizing bioactive molecules and specialty materials.
Later, derivatives such as imidazolidinyl urea became widely adopted in cosmetic and personal care products as preservatives due to their antimicrobial properties.
Today, Imidazolidone (2-imidazolidone) remains a significant building block in chemical synthesis, benefiting from ongoing research in medicinal chemistry and material science.
Stability and Reactivity of Imidazolidone (2-Imidazolidone):
Chemical stability:
Imidazolidone (2-imidazolidone) is chemically stable under normal conditions of use, handling, and storage.
Reactivity:
Imidazolidone (2-imidazolidone) exhibits low reactivity.
Imidazolidone (2-imidazolidone) may react with strong oxidizing agents.
Conditions to avoid:
Excessive heat.
Direct sunlight.
Contact with strong oxidizers.
Incompatible materials:
Strong oxidizing agents.
Strong acids.
Strong bases.
Hazardous decomposition products:
Thermal decomposition may produce nitrogen oxides (NOx).
Carbon monoxide (CO) may form.
Carbon dioxide (CO₂) may be generated.
Handling and Storage of Imidazolidone (2-Imidazolidone):
Handling:
Handle in accordance with good industrial hygiene and safety practices.
Avoid inhalation of dust.
Avoid contact with eyes.
Storage:
Store in a cool, dry, and well-ventilated area.
Keep containers tightly closed when not in use.
Storage conditions:
Protect from moisture.
Protect from excessive heat.
Packaging materials:
Store in inert, tightly sealed containers.
Shelf life:
Stable for extended periods when stored under recommended conditions.
First Aid Measures of Imidazolidone (2-Imidazolidone):
Inhalation:
Remove person to fresh air.
Seek medical attention if irritation or symptoms persist.
Skin contact:
Wash skin thoroughly with soap and water.
Remove contaminated clothing if necessary.
Eye contact:
Rinse cautiously with water for several minutes.
Remove contact lenses if present and easy to do.
Seek medical attention if irritation persists.
Ingestion:
Rinse mouth with water.
Seek medical advice if large amounts are ingested or discomfort occurs.
Most important symptoms:
Mild irritation to eyes.
Mild irritation to skin.
Respiratory tract irritation due to dust exposure.
Firefighting Measures of Imidazolidone (2-Imidazolidone):
Suitable extinguishing media:
Water spray.
Foam.
Dry chemical powder.
Carbon dioxide (CO₂).
Specific hazards:
May release toxic fumes such as nitrogen oxides.
Carbon oxides may also be released.
Protective equipment for firefighters:
Wear self-contained breathing apparatus.
Wear full protective clothing.
Special precautions:
Avoid inhalation of fumes.
Control dust formation during firefighting.
Accidental Release Measures of Imidazolidone (2-Imidazolidone):
Personal precautions:
Avoid breathing dust.
Use appropriate personal protective equipment.
Environmental precautions:
Prevent large quantities from entering drains or watercourses.
Methods for cleanup:
Sweep or vacuum spilled material using dust-minimizing methods.
Collect and dispose of according to local regulations.
Exposure Controls / Personal Protection of Imidazolidone (2-Imidazolidone):
Occupational exposure limits:
Not specifically established.
Engineering controls:
Adequate general ventilation is recommended.
Respiratory protection:
Use dust mask if airborne particles are generated.
Hand protection:
Use protective gloves for prolonged contact.
Eye protection:
Use safety glasses or goggles.
Skin protection:
Wear protective clothing to minimize contact.
Hygiene measures:
Wash hands after handling.
Avoid eating, drinking, or smoking in work areas.
Identifiers of Imidazolidone (2-Imidazolidone):
CAS No.: 120-93-4
Chemical Name: 2-Imidazolidone (2-imidazolidone)
CBNumber: CB5363122
Molecular Formula: C3H6N2O
Molecular Weight: 86.09
MDL Number: MFCD00005257
Product Number: I0005
Purity / Analysis Method : >97.0%(GC)
Molecular Formula / Molecular Weight: C3H6N2O = 86.09
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 120-93-4
Reaxys Registry Number: 106252
PubChem Substance ID: 87571415
SDBS (AIST Spectral DB): 2265
Merck Index (14): 4914
MDL Number: MFCD00005257
Empirical Formula (Hill Notation): C3H6N2O
CAS Number: 120-93-4
Molecular Weight: 86.09
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24896082
EC Number: 204-436-4
Beilstein/REAXYS Number: 106252
MDL number: MFCD00005257
Assay: 96%
CAS: 120-93-4
IUPAC Name: imidazolidin-2-one
Molecular Formula: C3H6N2O
InChI Key: YAMHXTCMCPHKLN-UHFFFAOYSA-N
SMILES: O=C1NCCN1
Molecular Weight (g/mol): 86.09
MDL Number: MFCD00005257
CAS Number: 120-93-4
ChEBI: CHEBI:37001
ChEMBL: ChEMBL12034
ChemSpider: 8142
ECHA InfoCard: 100.004.034
EC Number: 204-436-4
PubChem CID: 8453
UNII: 2K48456N55
CompTox Dashboard (EPA): DTXSID0020602
InChI: InChI=1S/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)
Key: YAMHXTCMCPHKLN-UHFFFAOYSA-N
SMILES: O=C1NCCN1
Properties of Imidazolidone (2-Imidazolidone):
Chemical formula: C3H6N2O
Molar mass: 86.094 g·mol−1
Appearance: White to off-white crystalline solid
Density: 1.15 g/cm3
Melting point: 129–132 °C
Solubility in water: Soluble in water and methanol
Quality Level: 200
assay: 96%
mp: 129-132 °C (lit.)
SMILES string: O=C1NCCN1
InChI: 1S/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)
InChI key: YAMHXTCMCPHKLN-UHFFFAOYSA-N
Melting point: 129-132 °C (lit.)
Boiling point: 158.75°C (rough estimate)
Density: 1.1530 (rough estimate)
vapor pressure: 0.002Pa at 20℃
refractive index: 1.5110 (estimate)
Flash point: 265°C
storage temp.: Sealed in dry,Room Temperature
form: Powder or Crystalline Powder
pka: 14.58±0.20(Predicted)
color: White to off-white
Odor: odorless
Water Solubility: soluble
Merck: 14,4914
BRN: 106252
Melting Point: 132 °C
Solubility in water: Soluble
Degree of solubility in water: 950 g/l 20 °C
Solubility (soluble in): Methanol
Solubility (slightly sol. in): Ether, Chloroform
Molecular Weight: 86.09 g/mol
XLogP3: -1.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 86.048012819 Da
Monoisotopic Mass: 86.048012819 Da
Topological Polar Surface Area: 41.1 Ų
Heavy Atom Count: 6
Complexity: 63.2
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of Imidazolidone (2-Imidazolidone):
Appearance: White to Almost white powder to crystal
Purity(GC): min. 97.0 %
Melting point: 131.0 to 136.0 °C
Appearance (Color): White to light yellow
Appearance (Form): Powder
Infrared spectrum: Conforms
HPLC: >=95.0 %
Names of Imidazolidone (2-Imidazolidone):
Preferred IUPAC name:
Imidazolidin-2-one
Other names:
Ethyleneurea
2-Imidazolidone
imidazolidin-2-one
1,3-ethyleneurea
