616-04-6

Basic information

• Product Name: 1-METHYLHYDANTOIN
• Synonyms: 1-Methyl-2,4-imidazolidinedione;Dioxy-creatinine;Hydantoin, 1-methyl-;1-METHYLHYDANTOIN;1-methyldiazolidine-2,4-dione;1-Methylhydantoine;1-methylimidazolidine-2,4-dione;N-Methylhydantoin
• CAS NO: 616-04-6
• Molecular Formula: C₄H₆N₂O₂
• Molecular Weight: 114.1
• EINECS: 210-460-6
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 616-04-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 156-157 °C(lit.)
• Boiling Point: 213.59°C (rough estimate)
• Appearance: white fine crystalline powder
• Density: 1.284
• Refractive Index: 1.4487 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.94±0.10(Predicted)
• Water Solubility: Soluble in methanol. (almost transparency). Insoluble in water.
• CAS DataBase Reference: 1-METHYLHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLHYDANTOIN(616-04-6)
• EPA Substance Registry System: 1-METHYLHYDANTOIN(616-04-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 616-04-6(Hazardous Substances Data)

Usage

Chemical Properties

WHITE FINE CRYSTALLINE POWDER

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

Definition

ChEBI: A imidazolidine-2,4-dione that is the N-methyl-derivative of hydantoin.

Metabolic pathway

The metabolic pathway of 1-methylhydantoin via 5-hydroxy-1-methylhydantoin, methylparabanic acid, and 5-N-methyloxaluric acid proves to be a major and general metabolic pathway in rabbits.

InChI:InChI=1/C4H6N2O2/c1-6-3(7)2-5-4(6)8/h2H2,1H3,(H,5,8)

Upstream product

• 111184-59-9 3-methylhydantoic acid nitrile 
• 30565-25-4 N-carbamoylsarcosine 
• 57-00-1 Creatinine 
• 107-97-1 sarcosine 
• 506-77-4 cyanogen chloride 
• 60-27-5 Creatinine 
• 60-27-5 creatinine 
• 131543-46-9 Glyoxal 
• 598-50-5 N-Methylurea 
• 111184-52-2 3-methylhydantoinamide 
• 84210-26-4 1-methyl-5-hydroxy-imidazoline-2,4-dione 
• 104892-31-1 (1-Methyl-ureido)-acetic acid ethyl ester 
• 111184-53-3 N-Methyl-2-(1-methyl-ureido)-acetamide 
• 57-13-6 urea 

Downstream Products

• 55441-71-9 9-methyluric acid 
• 31113-70-9 5-(benzylidene)-1-methylhydantoin 
• 349104-55-8 3-[2-(3,4-Dimethoxy-phenyl)-ethyl]-1-methyl-imidazolidine-2,4-dione 
• 198064-26-5 3-[3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propyl]-1-methyl-2,4-imidazolidinedione 
• 1028091-05-5 1-methyl-5-[1-(2-pyrrolidin-1-yl-phenyl)-methyl(Z)-ylidene]-imidazolidine-2,4-dione 
• 1028091-07-7 1-methyl-5-[1-(2-pyrrolidin-1-yl-phenyl)-methy-(E)-ylidene]-imidazolidine-2,4-dione 
• 1251039-19-6 C₁₄H₁₆N₄O₄ 
• 2221-12-7 1-methyl-3-phenyl-2,4-imidazolidinedione 
• 1432728-61-4 4-(4-fluorophenyl)-7-[(3-methyl-2,5-dioxoimidazolidin-1-yl)methyl]quinoline-2-carbonitrile 
• 1401066-00-9 3-(4-methoxybenzyl)-1-methylimidazolidine-2,4-dione 

Relevant articles and documents

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”

Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C-90°C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.

AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES

The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.

Facile synthesis of hydantoins and thiohydantoins in aqueous solution

A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.