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:

98%,99%, ^*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
• Uses: A metabolite of Mephenytoin A metabolite of Mephenytoin. This molecule has been shown to bind to voltage-dependent sodium channels (NVSC) and has antiepileptic properties.

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

• 1、 -. "Method for continuously and quickly preparing DL-phenylglycine and analogue thereof". Paragraph 0025; 0028. . Retrieved 2019/07/04.
• 2、 Vukeli?, Stella,Koksch, Beate,Seeberger, Peter H.,Gilmore, Kerry. "A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins". supporting information. p. 13451 - 13454. Retrieved 2016/09/13.