26975-70-2

Basic information

• Product Name: 2-amino-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one
• Synonyms: 4H-imidazol-4-one, 2-amino-3,5-dihydro-5,5-diphenyl-; 4-imidazolidinone, 2-imino-5,5-diphenyl-
• CAS NO: 26975-70-2
• Molecular Formula: C₁₅H₁₃N₃O
• Molecular Weight: 251.2832
• Mol File: 26975-70-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 417.6°C at 760 mmHg
• Flash Point: 206.3°C
• Density: 1.27g/cm³
• Vapor Pressure: 3.5E-07mmHg at 25°C
• Refractive Index: 1.666
• CAS DataBase Reference: 2-amino-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one(26975-70-2)
• EPA Substance Registry System: 2-amino-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one(26975-70-2)

Safety Data

• Hazardous Substances Data: 26975-70-2(Hazardous Substances Data)

Usage

Classification

Benzodiazepine derivative

Properties

Sedative
Anxiolytic (anti-anxiety)
Muscle relaxant

Mechanism of Action

Enhances the effects of the neurotransmitter gamma-aminobutyric acid (GABA) in the brain
Results in reduced anxiety and muscle tension

Uses

Calming effects on the central nervous system
Used in research settings to study its effects on the central nervous system
Potential therapeutic application in the treatment of:
Anxiety disorders
Muscle spasms

Caution

Should be handled and used with caution due to potential for abuse and addiction.

Upstream product

• 113-00-8 guanidine nitrate 
• 134-81-6 benzil 
• 3060-50-2 2,2-diphenylglycine 
• 133910-40-4 N-carbobenzoxy-2,2-diphenylglycylcyanamide sodium salt 
• 95166-02-2 N-carbobenzyloxy-2,2-diphenylglycine 
• 593-85-1 diguanidine carbonate 
• 133910-41-5 N-carbobenzoxy-5,5-diphenyl-2-iminohydantoin 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 58030-75-4 1-(2,6-dimethyl-phenyl)-3-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-urea 
• 26975-80-4 2-amino-3-methyl-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one 
• 14252-56-3 2-amino-3-benzyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one 

Relevant articles and documents

Synthesis of hydantoins, thiohydantoins, and glycocyamidines under solvent-free conditions

Hydantoins, thiohydantoins, and glycocyamidines have been prepared in moderate to excellent yields at room temperature under solvent-free conditions. 3N-amino and carboamide derivatives of hydantoin (7-8) were prepared in single step by condensing benzil with semicarbazide and biuret respectively.

Synthesis and Anticonvulsant Activity of 2-Iminohydantoins

Iminohydantoins selectively substituted at position C-5 and their 1-carbobenzoxy derivatives have been synthesized, and their anticonvulsant activity was evaluated in mice.In general, the more lipophilic 1-carbobenzoxy iminohydantoins were more potent than the unsubstituted counterparts.Evaluation of the individual enantiomers of the chiral iminohydantoins showed that the anticonvulsant activity resided primarily in the S isomers.In this study, (S)-(+)-1-carbobenzoxy-5-isobutyl-2-iminohydantoin (9a) was the most active member.This compound was not nearly as active as phenythoin against electrically induced convulsions, but was also active against pentylenetetrazole-induced seizures, suggesting a broader clinical potential.The closest analogue of phenytoin, viz., 5,5-diphenyl-2-iminohydantoin (1), failed to show any significant activity.Methylation on N-3 or the imino nitrogen of 1 also did not provide a compound with substantial activity. 2-Thiophenytoin was not active against electoshock seizures and showed only a weak activity against pentylenetetrazole.This study suggested that the structure-activity relationship of 2-iminohydantoins was quite different from that of 2-hydantoins.

Derivatives of 5.5-diphenyl-glycocyamidine

Guanidine, p-toluenesulfonyl-guanidine or dicyandiamide react with benzil to give 5,5-diphenyl-glycocyamidines. The influence of the alkali concentration and the reaction time on the direction of the condensation is investigated. For 5,5-diphenyl-Nexo-p-toluenesulfonyl-glycocyamidine a structure proving synthesis is given.