5,5-Dimethylhydantoin

Base Information

• Chemical Name: 5,5-Dimethylhydantoin
• CAS No.: 77-71-4
• Deprecated CAS: 25154-41-0,1689577-91-0
• Molecular Formula: C5H8N2O2
• Molecular Weight: 128.131
• Hs Code.: 2933.21
• European Community (EC) Number: 201-051-3
• NSC Number: 8652
• UNII: 34032MQ9RO
• DSSTox Substance ID: DTXSID5021754
• Nikkaji Number: J25.257C
• Wikidata: Q27256302
• ChEMBL ID: CHEMBL3181806
• Mol file: 77-71-4.mol

Synonyms:5,5-dimethylhydantoin;5,5-dimethylhydantoin sodium salt

Chemical Property of 5,5-Dimethylhydantoin

Chemical Property:

• Appearance/Colour: white to off-white crystals or crystalline powder
• Melting Point: 174-177 °C(lit.)
• Refractive Index: 1.449
• Boiling Point: 237.54°C (rough estimate)
• PKA: pKa 8.1 (Uncertain)
• Flash Point: 193oC
• PSA: 58.20000
• Density: 1.142 g/cm³
• LogP: 0.26200
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: H2O: 0.1 g/mL hot, clear
• Water Solubility.: soluble
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.058577502
• Heavy Atom Count: 9
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

5,5-Dimethylhydantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CC1(C(=O)NC(=O)N1)C
• Uses: 5,5-Dimethylhydantoin is part of a group of hydantoin compounds that are being evaluated for their anticonvulsant and central nervous system antitumour properties.

Technology Process of 5,5-Dimethylhydantoin

There total 63 articles about 5,5-Dimethylhydantoin 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: 92.0%

potassium cyanate (590-28-3) + methyl 2-aminoisobutyrate hydrochloride (15028-41-8) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Guidance literature:

potassium cyanate; methyl 2-aminoisobutyrate hydrochloride; In water; Milling; Green chemistry;

With potassium carbonate; In water; Green chemistry;

DOI:10.1021/jo5017629

Reference yield: 82.0%

potassium cyanide + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) + acetone (67-64-1) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Guidance literature:

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

DOI:10.1055/s-0035-1560317

Reference yield: 62.5%

2,3:4,5-di-O-isopropylidene-D-xylose (3673-15-2,13039-93-5,13039-94-6,23568-31-2,50866-82-5,81801-10-7,120522-08-9,120522-09-0,120522-10-3) → 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 5-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione (116730-53-1)

Guidance literature:

With potassium cyanide; In ethanol; water; at 50 ℃; for 24h;

DOI:10.1016/0008-6215(88)84147-8

upstream raw materials:

3,4-dihydro-4,4,6-trimethylpyrimidine-2(1H)-thione

2-amino-2-methylpropanamide

2-cyano-2-methylpropanamide

(1-Cyan-1-methylethyl)harnstoff

Downstream raw materials:

3-isopropyl-5,5-dimethylhydantoin

4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

3-{(3E)(2S)-3-aza-2-[(4-bromophenyl)methyl]-4-(4-methoxyphenyl)but-3-enyl}-5,5-dimethyl-1,3-diazolidine-2,4-dione

5,5-dimethyl-3-(p-tolyl)imidazolidine-2,4-dione

Refernces

• 1、 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.
• 2、 Konnert, Laure,Reneaud, Benjamin,De Figueiredo, Renata Marcia,Campagne, Jean-Marc,Lamaty, Frdric,Martinez, Jean,Colacino, Evelina. "Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin". . p. 10132 - 10142. Retrieved 2015/02/19.