1,3-Dihydroimidazol-2-one NEW

Technical Analysis and Industrial Applications of 1,3-Dihydroimidazol-2-one (CAS No.: 5918-93-4) – A Multifunctional Heterocyclic Compound

I. Basic Information and Physicochemical Properties

1. Core Chemical Parameters

• Chinese Name: 1,3-Dihydroimidazol-2-one

• English Name: 1,3-Dihydroimidazol-2-one

• Synonyms: Hydantoin, 2,4-Imidazolidinedione

• CAS No.: 5918-93-4

• Molecular Formula: $C_3{H}_4{N}_2{O}_2$

• Molecular Weight: 100.08

• Appearance: White to off-white crystalline powder, odorless, bitter taste.

2. Physicochemical Properties

• Acidity/Basicity: Weakly acidic amide bond (pKa≈7.8), forms salts with strong bases (e.g., sodium hydantoin).

• Reactivity:

• Stability: Stable at room temperature; hydrolyzes under high heat or strong acid conditions.

• Nitrogen atoms at positions 1 and 3 undergo alkylation/acylation to form N-substituted hydantoins.

• Carbonyl group at position 2 participates in nucleophilic additions, a key site for heterocycle derivative synthesis.

• Melting Point: 218-220℃ (decomposes)

• Boiling Point: 412℃ (atmospheric pressure)

• Density: 1.41 g/cm³

• Solubility: Slightly soluble in cold water (~1.2g/100mL at 25℃), soluble in hot water, methanol, ethanol, and dilute alkaline solutions; insoluble in non-polar solvents (e.g., ether, benzene).

• Chemical Characteristics:

II. Upstream and Downstream Industrial Chain Analysis

1. Upstream Raw Materials and Synthesis Processes

• Cyclization Method:
  Urea reacts with ethylene glycol under acidic catalysis (e.g., HCl) at 150-180℃ to form crude 1,3-dihydroimidazol-2-one. Purification via alkali dissolution, acidification, and recrystallization (water/ethanol system) yields ≥99% purity product with 75-80% yield.
  Reaction Equation:
  $N{H}_{2}CON{H}_2+HOC{H}_{2}C{H}_{2}OH\underset{△}{\overset{H^{+}}{\to }}{C}_3{H}_4{N}_2{O}_2+2H_{2}O$

• Urea (CAS: 57-13-6)

• Ethylene glycol (CAS: 107-21-1)/Glycolic acid (CAS: 79-14-1)

• Core Raw Materials:

• Mainstream Synthesis Route:

2. Downstream Products and Derivatives

• Ligand for Metal-Organic Frameworks (MOFs) materials.

• Synthesis of controlled-release drug carriers and biodegradable polymers.

• Synthesis of imidazolinone herbicides (e.g., metamifop, imazethapyr intermediates).

• Development of insect growth regulators (e.g., chitin synthesis inhibitor intermediates).

• Synthesis of antiepileptic drugs (e.g., phenytoin sodium, hydantoin derivatives) and antivirals (e.g., acyclovir intermediates).

• Production of novel immunomodulators (e.g., JAK kinase inhibitor intermediates).

• Pharmaceutical Intermediates:

• Agrochemical Intermediates:

• Materials and Fine Chemicals:

III. Key Application Fields

1. Pharmaceutical R&D and Innovative Drugs

• Antiepileptic Drug Intermediate:
  Condensation with benzaldehyde yields 5-phenylhydantoin, a precursor for phenytoin sodium. By inhibiting neuronal sodium channels and stabilizing membrane potentials, it remains a first-line treatment for tonic-clonic seizures for over 70 years.

• Antiviral Drug Precursor:
  Reacts with ribonucleosides to produce nucleoside analogs (e.g., acyclovir intermediates), blocking herpesvirus replication via DNA polymerase inhibition.

• Anticancer Drug Synthesis:
  Serves as a heterocycle scaffold in histone deacetylase (HDAC) inhibitors, regulating gene expression to suppress tumor growth (applicable to leukemia, lymphoma).

2. Agrochemical Innovation and Green Pest Control

• High-Efficiency Herbicide Intermediate:
  Condenses with chloropyridine to form metamifop intermediates, selectively controlling annual grasses and broadleaf weeds in soy/corn fields at 20-30g/ha, with low residue and crop safety.

• Novel Insecticide Development:
  Methoxy-substituted imidazolinones inhibit chitin synthesis, disrupting insect molting, achieving >90% efficacy against lepidopteran larvae with eco-friendly properties.

3. Materials Science and Biomedicine

• MOFs Ligand:
  Coordinates with Zn²⁺, Cu²⁺ to form high-surface-area MOFs for CO₂ adsorption (1.5mmol/g capacity) and drug controlled release (targeted anticancer delivery).

• Biodegradable Materials:
  Copolymerizes with lactic acid to enhance PLA mechanical properties and degradation rates for surgical sutures and tissue engineering scaffolds.

IV. Technological Advantages and Market Dynamics

• Technical Barriers:
  Cyclization requires precise control of feed ratios and temperature. Microwave-assisted synthesis reduces reaction time to 2 hours, boosting yield to 85% with <0.1% impurities.

• Capacity Distribution:
  Global annual capacity ~200 tons, 65% in China. Major producers include Shandong Xinhua Pharmaceutical, Jiangsu Lianhua Technology, primarily using urea-ethylene glycol cyclization. Some adopt green solvents (e.g., ionic liquids) to replace traditional acid catalysis.

• Market Demand:
  Driven by demand for antiepileptics, novel agrochemicals, and biomaterials, 2024 demand grew 16% YoY. 2025 market size is projected to exceed $40 million, with pharmaceuticals accounting for 70%.

V. Safety and Storage Recommendations

• Hazards:
  Dust irritates eyes and respiratory tract. Rat oral LD50＞2000mg/kg (low toxicity). Wear dust masks and gloves; avoid inhalation or skin contact.

• Storage Conditions:
  Store in sealed, cool, dry conditions (≤25℃) using moisture-proof packaging (e.g., aluminum foil bags or cardboard drums with PE liners). Keep away from strong oxidizers and acids. Shelf life: 2 years.

VI. SEO Optimization Strategy

1. Keyword Layout

• Core Keywords: 1,3-Dihydroimidazol-2-one, 5918-93-4, Hydantoin, antiepileptic drug intermediate, imidazolinone herbicide

• Long-Tail Keywords: Hydantoin synthesis process, phenytoin sodium raw material, biodegradable material intermediate

• Chinese-English Combinations: 1,3-Dihydroimidazol-2-one, Hydantoin, CAS 5918-93-4

Formatted to maintain technical accuracy, structural clarity, and SEO-friendly keyword integration.