1-Methylhydantoin

Base Information

• Chemical Name: 1-Methylhydantoin
• CAS No.: 616-04-6
• Molecular Formula: C4H6N2O2
• Molecular Weight: 114.104
• Hs Code.: 29332100
• European Community (EC) Number: 210-460-6
• NSC Number: 80560
• UNII: 0546H9UR1R
• DSSTox Substance ID: DTXSID90210595
• Nikkaji Number: J100.995H
• Wikidata: Q27101864
• Metabolomics Workbench ID: 38380
• ChEMBL ID: CHEMBL4758352
• Mol file: 616-04-6.mol

Synonyms:1-methylhydantoin;N-methylhydantoin

Chemical Property of 1-Methylhydantoin

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Melting Point: 156-157 °C(lit. )
• Refractive Index: 1.491
• Boiling Point: 213.59°C (rough estimate)
• PKA: 8.94±0.10(Predicted)
• PSA: 49.41000
• Density: 1.284 g/cm³
• LogP: -0.56530
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol. (almost transparency). Insoluble in water.
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.042927438
• Heavy Atom Count: 8
• Complexity: 143

Purity/Quality:

99.5% ^*data from raw suppliers

1-Methylhydantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CC(=O)NC1=O
• Uses: Reactant for organocatalytic tandem three component reactions of aldehyde, alkyl vinyl ketone, and amideReactant for synthesis of:Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibitionAllosteric glucokinase activatorsHydantoin derivatives with antiproliferative activityThiohydantoinsP2X7 receptor antagonists

Technology Process of 1-Methylhydantoin

There total 28 articles about 1-Methylhydantoin 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%

1-methyl-5-hydroxy-imidazoline-2,4-dione (84210-26-4,680974-15-6) → 1-methyldiazolidine-2,4-dione (616-04-6)

Guidance literature:

With iodic acid; at 60 ℃; for 0.5h;

DOI:10.1039/P19890001153

Reference yield: 87.0%

thiosemicarbazide (79-19-6) + mono-N-methyl-4,5-dihydroxyimidazolidin-2-one (22322-62-9) → 1-methyl-4,5-bis(3-thiosemicarbazido)imidazolidin-2-one + 1-methyldiazolidine-2,4-dione (616-04-6)

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 1h; pH=2;

DOI:10.1007/s11172-006-0344-6

Reference yield: 85.0%

(1-Methyl-ureido)-acetic acid ethyl ester (104892-31-1) → 1-methyldiazolidine-2,4-dione (616-04-6)

Guidance literature:

With sodium methylate; In methanol;

upstream raw materials:

creatinine

potassium cyanate

sarcosine

N-carbamoyl-alanine ethyl ester

Downstream raw materials:

9-methyluric acid

5-(benzylidene)-1-methylhydantoin

1-Methyl-5-[1-(5-methyl-2-nitro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione

(Z)-1-methyl-5-(4-nitrophenyl)methylenehydantoin

Refernces

• 1、 Hitchcock, Daniel S.,Fedorov, Alexander A.,Fedorov, Elena V.,Almo, Steven C.,Raushel, Frank M.. "Discovery of a bacterial 5-methylcytosine deaminase". . p. 7426 - 7435. Retrieved 2015/04/16.
• 2、 Lu, Haibin,Kong, Dejuan,Wu, Bin,Wang, Shihan,Wang, Yongsheng. "Synthesis and evaluation of anti-inflammatory and antitussive activity of hydantion derivatives". experimental part. p. 638 - 642. Retrieved 2012/08/28.