5-Methyl-5-phenylhydantoin

Base Information

• Chemical Name: 5-Methyl-5-phenylhydantoin
• CAS No.: 6843-49-8
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.202
• Hs Code.: 29332100
• European Community (EC) Number: 229-928-6
• NSC Number: 14839
• UNII: R5C75HK8E7
• DSSTox Substance ID: DTXSID201311373
• Nikkaji Number: J103.873G
• ChEMBL ID: CHEMBL3546317
• Mol file: 6843-49-8.mol

Synonyms:5-methyl-5-phenylhydantoin;5-methyl-5-phenylhydantoin, (+-)-isomer;5-methyl-5-phenylhydantoin, (R)-isomer;5-methyl-5-phenylhydantoin, (S)-isomer;5-methyl-5-phenylhydantoin, 4-11C-labeled;5-methyl-5-phenylhydantoin, monosodium salt;5-methyl-5-phenylhydantoin, monosodium salt, monohydrate

Chemical Property of 5-Methyl-5-phenylhydantoin

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 199-201 °C(lit.)
• Refractive Index: 1.505
• Boiling Point: 325.7°C (rough estimate)
• PKA: 8.60±0.10(Predicted)
• Flash Point: 9℃
• PSA: 58.20000
• Density: 1.216 g/cm³
• LogP: 1.39880
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 190.074227566
• Heavy Atom Count: 14
• Complexity: 271

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Methyl-5-phenylhydantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(=O)NC(=O)N1)C2=CC=CC=C2
• Uses: 5-Methyl-5-phenylhydantoin is a reactant for synthesis of beta-amino alcohols as inhibitors of anti-tubercular target N-acetyltransferase, chlorohydantoins and specific MMP inhibitors.

Technology Process of 5-Methyl-5-phenylhydantoin

There total 16 articles about 5-Methyl-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: 91.0%

potassium cyanide + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) + acetophenone (98-86-2) → 5-methyl-5-phenylimidazolidin-2,4-dione (6843-49-8,27539-12-4,99571-24-1,101693-73-6)

Guidance literature:

In water; ethyl acetate; at 120 ℃; for 0.533333h; under 15001.5 Torr; Solvent; Flow reactor;

DOI:10.1055/s-0035-1560317

Reference yield: 90.0%

carbon dioxide (124-38-9,18923-20-1) + α-amino-α-methylphenylacetonitrile (4355-46-8) → 5-methyl-5-phenylimidazolidin-2,4-dione (6843-49-8,27539-12-4,99571-24-1,101693-73-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 20h;

DOI:10.1039/b719675j

Reference yield: 59.0%

hydrogen cyanide (74-90-8) + carbon dioxide (124-38-9,18923-20-1) + acetophenone (98-86-2) → 5-methyl-5-phenylimidazolidin-2,4-dione (6843-49-8,27539-12-4,99571-24-1,101693-73-6)

Guidance literature:

acetophenone; With gallium(III) triflate; ammonia; In dichloromethane; at -78 ℃; for 3h; Inert atmosphere;

hydrogen cyanide; In dichloromethane; at -78 - 25 ℃; Inert atmosphere;

carbon dioxide; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 5h; Inert atmosphere;

DOI:10.1039/b719675j

upstream raw materials:

acetophenone

ammonium bicarbonate

hydrogen cyanide

carbon dioxide

Downstream raw materials:

2-phenyl-2-phthalimidopropionic acid

(S)-2-methyl-2-phenylglycine

(S)-5-methyl-5-phenyl-2,4-imidazolidinedione

3-(3-chloropropyl)-5-methyl-5-phenylimidazolidine-2,4-dione

Refernces

• 1、 Kucwaj-Brysz, Katarzyna,Kurczab, Rafa?,Jastrz?bska-Wi?sek, Magdalena,?es?awska, Ewa,Sata?a, Grzegorz,Nitek, Wojciech,Partyka, Anna,Siwek, Agata,Jankowska, Agnieszka,Weso?owska, Anna,Kie?-Kononowicz, Katarzyna,Handzlik, Jadwiga. "Computer-aided insights into receptor-ligand interaction for novel 5-arylhydantoin derivatives as serotonin 5-HT7 receptor agents with antidepressant activity". . p. 102 - 114. Retrieved 2018/02/10.
• 2、 Monteiro, Julia L.,Pieber, Bartholom?us,Corrêa, Arlene G.,Kappe, C. Oliver. "Continuous Synthesis of Hydantoins: Intensifying the Bucherer-Bergs Reaction". supporting information. p. 83 - 87. Retrieved 2015/12/26.