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

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 89-24-7 differently. You can refer to the following data:
1. A metabolite of Mephenytoin
2. A metabolite of Mephenytoin. This molecule has been shown to bind to voltage-dependent sodium channels (NVSC) and has antiepileptic properties.

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

• 538-51-2 benzylidene phenylamine 
• 1074-12-0 phenylglyoxal hydrate 
• 57-13-6 urea 
• 7647-01-0 hydrogenchloride 
• 590-28-3 potassium cyanate 
• 150-30-1 Phenylalanine 
• 37534-65-9 D-2-carbamoylamino-3-phenylpropionic acid 
• 100647-18-5 2-phenyl-2-ureidoacetamide 
• 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 

Downstream Products

• 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 
• 2062-22-8 C₃NH₂(C₆H₅)O₂NSCFCl₂ 
• 554-68-7 triethylamine hydrochloride 
• 3530-82-3 5-benzyl-hydantoin 
• 18744-13-3 1,1'-dimethyl-4,4'-diphenyl-tetrahydro-[4,4']biimidazolyl-2,5,2',5'-tetraone 
• 109758-03-4 3-[3-(4-Benzhydryl-piperazin-1-yl)-propyl]-5-phenyl-imidazolidine-2,4-dione 
• 82264-50-4 N-carbamoyl-D,L-phenylglycine 
• 614-22-2 1-benzoylurea 
• 15900-38-6 5-hydroxy-5-phenyl-imidazolidine-2,4-dione 

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.