Quick Search
Hydantoin, 5,5-Dimethyl- is a substituted five-membered heterocyclic imide more commonly known as 5,5-Dimethylhydantoin or DMH.
Hydantoin, 5,5-Dimethyl- is a key industrial intermediate used primarily in the production of N-halogenated hydantoin biocides for water treatment and disinfection applications.
Hydantoin, 5,5-Dimethyl- is also used in organic synthesis, silver electroplating, resin manufacturing, and as a building block in pharmaceutical and agrochemical research.
CAS Number: 77-71-4
EC Number: 201-051-3
Molecular Formula: C5H8N2O2
Molecular Weight: 128.13 g/mol
Synonyms: 5,5-Dimethylhydantoin, DMH, Hydantoin, 5,5-Dimethyl-, 5,5-Dimethylimidazolidine-2,4-dione, 4,4-Dimethyl-2,5-dioxoimidazolidine, 4-Imidazolidinedione, 5,5-Dimethyl-2-, 5,5-Dimethyl-4-Imidazolidinedione, Acetonylurea, Dantoin DMH, Equinox Stabilizer 15, DMH Water Treatment Chemical, UNII-34032MQ9RO, MFCD00005266, Beilstein 2827, PubChem CID 6491, EC 201-051-3, dantoindmh, 5,5-Dimethyl-Hydantoin
APPLICATIONS
Hydantoin, 5,5-Dimethyl- is used as the key precursor in the manufacture of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH), a widely used chlorine-donor biocide for water disinfection.
Hydantoin, 5,5-Dimethyl- is used as the precursor in the manufacture of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), a bromine-donor biocide employed in similar disinfection applications.
Hydantoin, 5,5-Dimethyl- is used in the formulation of slow-release chlorinating and brominating tablets and granules for swimming pools and spas.
Hydantoin, 5,5-Dimethyl- is used in cooling-tower and industrial water-treatment systems as the parent structure for biocidal compounds that control bacterial, algal, and fungal growth.
Hydantoin, 5,5-Dimethyl- is used in municipal and industrial water-treatment research as a stable, low-toxicity biocide precursor compared to older disinfection chemistries.
Hydantoin, 5,5-Dimethyl- is used in recirculating water systems, humidifiers, and evaporative cooling equipment where controlled, sustained biocide release is required.
Hydantoin, 5,5-Dimethyl- is used in the paper and pulp industry as a component of slimicide formulations for controlling microbial fouling in process water.
Hydantoin, 5,5-Dimethyl- is used in oilfield water-injection and produced-water treatment systems to control microbially induced corrosion and biofouling.
Hydantoin, 5,5-Dimethyl- is used as a cyanide-free additive in silver electroplating baths, offering an alternative to traditional cyanide-based plating chemistries.
Hydantoin, 5,5-Dimethyl- is used in electroplating research to improve deposit brightness, uniformity, and bath stability in precious-metal plating processes.
Hydantoin, 5,5-Dimethyl- is used in metal-finishing formulations requiring a stable, water-soluble organic additive.
Hydantoin, 5,5-Dimethyl- is used in specialty plating-bath development where reduced cyanide handling and disposal requirements are desired.
Hydantoin, 5,5-Dimethyl- is used as a reactant and starting material for the synthesis of N-chloroheterocyclic antimicrobial compounds in medicinal chemistry research.
Hydantoin, 5,5-Dimethyl- is used in the synthesis of beta-amino alcohols investigated as inhibitors of antitubercular drug targets.
Hydantoin, 5,5-Dimethyl- is used in the synthesis of second-generation inhibitors of hepatitis C virus NS3 serine protease in pharmaceutical research.
Hydantoin, 5,5-Dimethyl- is used as a reactant in asymmetric chlorolactonization reactions and other halogenation-based synthetic methodologies.
Hydantoin, 5,5-Dimethyl- is used as an intermediate in amino acid synthesis, including routes to alpha-methylalanine and related non-proteinogenic amino acids.
Hydantoin, 5,5-Dimethyl- is used in the production of specialty epoxy resins and water-soluble resins requiring a heterocyclic cross-linking or functional building block.
Hydantoin, 5,5-Dimethyl- is used as a monomer or comonomer precursor in specialty polymer and coating formulations valued for hydrolytic and thermal stability.
Hydantoin, 5,5-Dimethyl- is used in resin-additive research investigating hydantoin-based structures for improved chemical and UV resistance.
Hydantoin, 5,5-Dimethyl- is used in cosmetic and personal-care formulation research as a precursor to preservative-boosting hydantoin derivatives.
Hydantoin, 5,5-Dimethyl- is used in academic laboratories to demonstrate the Bucherer-Bergs reaction, in which acetone cyanohydrin and ammonium carbonate are combined to form the hydantoin ring.
Hydantoin, 5,5-Dimethyl- is used in heterocyclic chemistry teaching and research as a model substrate for studying hydantoin ring reactivity and halogenation chemistry.
Hydantoin, 5,5-Dimethyl- is used in analytical and reference-standard applications for environmental testing of hydantoin-derived biocide residues.
Hydantoin, 5,5-Dimethyl- is used as an analytical reference material in environmental monitoring programs assessing the fate and degradation of halogenated hydantoin biocides.
Hydantoin, 5,5-Dimethyl- is used in quality-control laboratories to verify raw-material purity ahead of downstream halogenation reactions.
Hydantoin, 5,5-Dimethyl- is used in research evaluating the environmental compatibility and comparative toxicity of hydantoin-based biocides relative to older disinfection chemicals.
Hydantoin, 5,5-Dimethyl- is used according to the purity grade and regulatory status appropriate to the intended water-treatment, industrial, cosmetic, or pharmaceutical application.
DESCRIPTION
Hydantoin, 5,5-Dimethyl- is a white to off-white crystalline powder or solid, typically supplied in high-purity form for industrial and research use.
Hydantoin, 5,5-Dimethyl- consists of a five-membered imidazolidine-2,4-dione (hydantoin) ring bearing two methyl substituents at the 5-position, giving the molecule its characteristic steric bulk and chemical stability.
Hydantoin, 5,5-Dimethyl- is typically manufactured via the Bucherer-Bergs reaction, in which acetone cyanohydrin is reacted with ammonium carbonate under mild heating to construct the hydantoin ring directly.
Hydantoin, 5,5-Dimethyl- is soluble in hot water and shows good solubility in polar organic solvents such as ethanol, acetone, DMSO, and chloroform, while showing more limited solubility in cold water.
Hydantoin, 5,5-Dimethyl- possesses two nitrogen-hydrogen bonds on the ring that are readily halogenated under standard conditions, forming N-chloro or N-bromo derivatives that serve as the active biocidal species in downstream products.
Hydantoin, 5,5-Dimethyl- has a reported acidity (pKa) of approximately 9.2, reflecting the relatively weak acidic character of its ring N-H protons.
Hydantoin, 5,5-Dimethyl- is chemically stable under normal storage and handling conditions, maintaining consistent performance across a range of formulation environments.
Hydantoin, 5,5-Dimethyl- exhibits low lipophilicity, with a reported log P value below zero, consistent with its polar, hydrogen-bonding ring structure.
Hydantoin, 5,5-Dimethyl- can appear as a degradation product of its halogenated derivatives, such as 1,3-dibromo-5,5-dimethylhydantoin, and has been detected as a residue on inadequately rinsed food-contact surfaces treated with such biocides.
Hydantoin, 5,5-Dimethyl- is generally regarded as having low acute toxicity and favorable environmental compatibility relative to many older biocidal and disinfection chemistries.
Hydantoin, 5,5-Dimethyl- combustibility is classified as a combustible solid, requiring standard precautions against ignition sources during handling and storage.
Hydantoin, 5,5-Dimethyl- is available in various purity grades, including technical, reagent, and high-purity analytical grades, depending on the intended downstream synthetic or water-treatment application.
Hydantoin, 5,5-Dimethyl- serves as the structural core for a broader family of N-halohydantoin biocides that combine the stability of the hydantoin ring with the antimicrobial reactivity of the halogen substituents.
Hydantoin, 5,5-Dimethyl- is recognized in the water-treatment industry for producing biocides that release active halogen more slowly and predictably than simple inorganic chlorinating or brominating agents.
Hydantoin, 5,5-Dimethyl- is supplied in various particle-size and purity grades suited to electroplating, resin, pharmaceutical, and water-treatment manufacturing requirements.
PROPERTIES
Chemical Formula: C5H8N2O2
Molecular Weight: 128.13 g/mol
Common Name: 5,5-Dimethylhydantoin (DMH)
CAS Number: 77-71-4
EC Number: 201-051-3
Appearance: White to off-white crystalline powder or solid
Odor: Odorless to faint
Solubility: Soluble in hot water; soluble in ethanol, acetone, DMSO, and chloroform
Melting Point: 174–178°C
Boiling Point: Approximately 313°C (759 mmHg, literature estimate)
pKa: Approximately 9.19
Log P: Approximately −0.48
Vapor Pressure: Very low (approximately 2.8 × 10⁻⁶ mmHg)
Flash Point: Approximately 193°C
Combustibility: Classified as a combustible solid
Stability: Stable under recommended storage conditions; N-H positions are readily halogenated to form active biocidal derivatives
Regulatory Status: Not classified as hazmat, antibiotic, or DEA-regulated in standard commercial listings; downstream halogenated derivatives carry their own hazard classifications
Storage Temperature: Room temperature, in a dry, sheltered location
Shelf Life: Approximately 24 months in original sealed packaging
FIRST AID
Inhalation
Remove to fresh air immediately if dust is inhaled.
Seek medical attention if coughing or respiratory irritation persists.
Keep the affected person at rest in a position comfortable for breathing.
Skin Contact
Wash immediately with plenty of soap and water.
Remove contaminated clothing and shoes before reuse.
Seek medical advice if irritation or redness persists.
Eye Contact
Rinse immediately and continuously with plenty of water for at least 15 minutes.
Remove contact lenses if present and easy to do so, then continue rinsing.
Seek medical attention if irritation persists.
Ingestion
Rinse mouth thoroughly with water; do not induce vomiting.
Seek medical attention if a significant quantity has been swallowed.
Never give anything by mouth to an unconscious person.
Note to Physicians
Treat symptomatically and provide supportive care.
No specific antidote is known; monitor for gastrointestinal irritation following significant ingestion.
Provide supportive care and observe the patient for delayed symptoms.
HANDLING AND STORAGE
Handling
Wear appropriate personal protective equipment, including gloves, safety goggles, and protective clothing.
Avoid generating and inhaling dust during handling and transfer operations.
Wash hands thoroughly after handling and before eating, drinking, or smoking.
Engineering Controls
Use local exhaust ventilation or general ventilation to control airborne dust levels.
Ensure adequate ventilation in areas where the material is weighed, blended, or transferred, particularly ahead of downstream halogenation reactions.
Personal Protection
Wear chemical-resistant gloves and safety goggles when handling the material or preparing halogenation reaction mixtures.
Use a face shield where splashing or dust generation is likely during bulk transfer or reaction charging.
Storage
Store in a cool, dry, sheltered area at room temperature, away from strong oxidizing agents and halogenating reagents.
Keep containers tightly closed and properly labeled at all times.
Protect from moisture and prolonged heat exposure to maintain product quality.
Material Compatibility
Avoid contact with strong oxidizers and halogen sources during storage, since these are the same reagents used to intentionally functionalize the material in controlled industrial processes.
Use containers and equipment constructed of materials compatible with the substance and its intended downstream reaction chemistry.
Spill and Leak Procedures
Sweep up spilled material carefully to avoid generating dust, and place in a suitable container for disposal.
Avoid contact with skin and eyes during clean-up operations.
Dispose of collected material in accordance with local, regional, and national chemical-waste regulations.
Decontamination
Clean spill areas with water to remove residue, avoiding dry sweeping methods that generate dust.
Place contaminated absorbents and cleaning materials in labeled waste containers for disposal.
Handling Precautions
Handle only in areas equipped with appropriate safety and containment measures, particularly where downstream halogenation is performed.
Maintain good industrial hygiene practices throughout handling and processing.
Follow the current safety data sheet and applicable chemical-handling regulations for both the base compound and its halogenated derivatives.
