89-24-7

Basic information

• Product Name: 5-Phenylhydantoin
• Synonyms: 5-PHENYLHYDANTOIN;4-Phenylimidazolidine-2,5-dione;Phenylhydantoin;5-Phenylhydantoin (100 mg);5-Phenyl-
• CAS NO: 89-24-7
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• EINECS: 201-890-5
• Product Categories: Hydantoins and Derivatives;Hydantoins & Derivatives;Metabolites & Impurities;Hydantoins & Derivatives, Metabolites & Impurities
• Mol File: 89-24-7.mol
• Article Data: 23

Chemical Properties

• Melting Point: 182°C
• Appearance: /
• Density: 1.276g/cm3
• Refractive Index: 1.569
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 8.58±0.10(Predicted)
• CAS DataBase Reference: 5-Phenylhydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Phenylhydantoin(89-24-7)
• EPA Substance Registry System: 5-Phenylhydantoin(89-24-7)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 89-24-7(Hazardous Substances Data)

Usage

Description

5-Phenylhydantoin is a white solid that is a metabolite of Mephenytoin, a drug used to treat epilepsy. It has been shown to bind to voltage-dependent sodium channels (NVSC) and possesses antiepileptic properties.

Uses

Used in Pharmaceutical Industry:
5-Phenylhydantoin is used as an active pharmaceutical ingredient for the development of antiepileptic drugs. Its ability to bind to voltage-dependent sodium channels (NVSC) makes it a potential candidate for the treatment of epilepsy and other seizure disorders.
Used in Research and Development:
5-Phenylhydantoin is used as a research compound to study the mechanisms of action of antiepileptic drugs and to develop new therapeutic agents with improved efficacy and safety profiles. Its role in binding to voltage-dependent sodium channels (NVSC) provides valuable insights into the development of novel anticonvulsant medications.
Used in Metabolism Studies:
As a metabolite of Mephenytoin, 5-Phenylhydantoin is used in metabolism studies to understand the metabolic pathways and enzyme activities involved in the breakdown and elimination of antiepileptic drugs. This information can help in optimizing drug dosages and minimizing side effects.
Used in Quality Control and Analysis:
5-Phenylhydantoin is used as a reference compound in the quality control and analysis of pharmaceutical products containing Mephenytoin or other related antiepileptic drugs. Its chemical properties and reactivity can be utilized to develop analytical methods for the accurate determination of drug concentrations in various matrices.

InChI:InChI=1/C9H8N2O2/c12-8-7(10-9(13)11-8)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12,13)

Upstream product

• 88169-89-5 2-phenyl-2-ureidoacetonitrile 
• 538-51-2 benzylidene phenylamine 
• 1074-12-0 phenylglyoxal hydrate 
• 57-13-6 urea 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 7647-01-0 hydrogenchloride 
• 151312-45-7 N-moc-phenylglycineamide 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 124-38-9 carbon dioxide 
• 532-28-5 (RS)-mandelonitrile 
• 622-46-8 carbamic acid phenyl ester 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 100-46-9 benzylamine 
• 506-87-6 ammonium carbonate 

Downstream Products

• 614-22-2 1-benzoylurea 
• 2062-22-8 C₃NH₂(C₆H₅)O₂NSCFCl₂ 
• 554-68-7 triethylamine hydrochloride 
• 1443523-40-7 C₂₁H₂₂N₂O₂ 
• 1443523-41-8 C₂₁H₂₈N₂ 
• 1443523-47-4 5-(3-methylbut-2-enyl)-5-phenyl-3-phenylmethyl-2,4-imidazolidinedione 
• 34658-65-6 3-benzyl-5-phenylimidazolidine-2,4-dione 
• 2835-06-5 phenylglycin 
• 1246250-66-7 3-(2-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)ethyl)-5-phenylimidazolidine-2,4-dione 
• 18744-13-3 1,1'-dimethyl-4,4'-diphenyl-tetrahydro-[4,4']biimidazolyl-2,5,2',5'-tetraone 
• 82264-50-4 N-carbamoyl-D,L-phenylglycine 
• 15900-38-6 5-hydroxy-5-phenyl-imidazolidine-2,4-dione 
• 6489-76-5 D-(-)-N-carbamoyl phenyl glycine 
• 875-74-1 (R)-phenylglycine 

Relevant articles and documents

MACROMOLECULAR COMPOSITIONS FOR BINDING SMALL MOLECULES

The present invention relates to a method for preparing a macromolecular composition comprising phenylglyoxaldehyde-derivatives. The invention also relates to the macromolecular compositions per se, and to methods of using the macromolecular compositions. The macromolecular compositions are useful for undergoing subsequent reactions with small molecules, for instance to remove such small molecules from a solution.

Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates

A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.

Continuous Synthesis of Hydantoins: Intensifying the Bucherer-Bergs Reaction

A continuous Bucherer-Bergs hydantoin synthesis utilizing intensified conditions is reported. The methodology is characterized by a two-feed flow approach to independently feed the organic substrate and the aqueous reagent solution. The increased interfacial area of the biphasic reaction mixture and the lack of headspace enabled almost quantitative conversions within ca. 30 minutes at 120 °C and 20 bar even for unpolar starting materials. In addition, a selective N(3)-monoalkylation of the resulting heterocycles under batch microwave conditions is reported yielding potential acetylcholinesterase inhibitors.