5-Phenylhydantoin

Base Information

• Chemical Name: 5-Phenylhydantoin
• CAS No.: 89-24-7
• Deprecated CAS: 27534-86-7
• Molecular Formula: C9H8 N2 O2
• Molecular Weight: 176.175
• Hs Code.: 2933210000
• European Community (EC) Number: 201-890-5
• NSC Number: 51847,40885,27302
• UNII: ZQL8E3X7HK
• DSSTox Substance ID: DTXSID30883267
• Nikkaji Number: J26.364H
• Wikidata: Q27888008
• Pharos Ligand ID: PMZTA8ZP3526
• ChEMBL ID: CHEMBL156406
• Mol file: 89-24-7.mol

Synonyms:5-phenylhydantoin;5-phenylhydantoin sodium;5-phenylhydantoin, (+-)-isomer;5-phenylhydantoin, (R)-isomer;5-phenylhydantoin, (S)-isomer

Chemical Property of 5-Phenylhydantoin

Chemical Property:

• Melting Point: 182°C
• Refractive Index: 1.569
• PKA: 8.58±0.10(Predicted)
• Density: 1.276g/cm3
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

5-Phenylhydantoin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(=O)NC(=O)N2
• General Description: 5-Phenylhydantoin and its derivatives, particularly 5-ethyl-5-phenyl-3-propylhydantoin, exhibit promising anticonvulsant properties with reduced sedative effects compared to phenytoin. Structural analysis suggests that their biological activity is influenced by crystal packing interactions, highlighting their potential as effective therapeutic agents for seizure disorders.

Technology Process of 5-Phenylhydantoin

There total 53 articles about 5-Phenylhydantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

carbon dioxide (124-38-9,18923-20-1) + (RS)-mandelonitrile (532-28-5,613-88-7) → 5-phenylimidazolidine-2,4-dione (89-24-7,27534-86-7)

Guidance literature:

With ammonia; ammonium bicarbonate; In water; at 120 ℃; for 0.05h; under 11251.1 Torr;

Reference yield: 95.0%

potassium cyanide + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) + benzaldehyde (100-52-7) → 5-phenylimidazolidine-2,4-dione (89-24-7,27534-86-7)

Guidance literature:

With iron(III) oxide; In neat (no solvent); at 70 ℃; for 0.283333h; Solvent; Temperature;

DOI:10.1016/j.crci.2013.06.005

Reference yield: 92.0%

1,3-di-tert-butyl-5-phenylimidazolidine-2,4-dione (1031685-24-1) → 5-phenylimidazolidine-2,4-dione (89-24-7,27534-86-7)

Guidance literature:

With methanesulfonic acid; In hexane; at 65 ℃; for 3.5h;

DOI:10.1021/ja802242h

upstream raw materials:

N-carbamoyl-D,L-phenylglycine

2-phenyl-2-ureidoacetonitrile

benzylidene phenylamine

benzaldehyde

Downstream raw materials:

(4-benzyl-2,5-dioxo-imidazolidin-1-yl)-acetic acid ethyl ester

4-phenyl-1,3-dihydro-imidazol-2-one

5-phenyl-3H-[1,3,4]oxadiazol-2-one

5-hydroxy-5-phenyl-imidazolidine-2,4-dione

Refernces

Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents

10.1007/s00706-012-0791-8

The study focuses on the synthesis, structural, and biological evaluation of four 5-phenylhydantoin derivatives as potential anticonvulsant agents. These compounds were designed with lipophilicities similar to phenytoin, a well-established anticonvulsant drug. The anticonvulsant activities of the synthesized derivatives were assessed in rats using subcutaneous and intravenous pentylenetetrazol seizure tests, and their potential sedative effects were measured through spontaneous locomotor activity tests. The X-ray analysis of three compounds provided insights into their crystal structures, suggesting a correlation between crystal packing interactions and their biological activities. The study found that 5-ethyl-5-phenyl-3-propylhydantoin demonstrated the most favorable pharmacological properties among the synthesized compounds, with anticonvulsant activity comparable to phenytoin and a lower risk of inducing sedation in rats. This indicates its potential as an effective anticonvulsant agent with fewer sedative side effects.