15414-89-8

Basic information

• Product Name: 1,3,5,5-tetramethylimidazolidine-2,4-dione
• Synonyms: 1,3-Dimethyl-5,5-dimethylhydantoin
• CAS NO: 15414-89-8
• Molecular Formula: C₇H₁₂N₂O₂
• Molecular Weight: 156.1824
• Mol File: 15414-89-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 187.1°C at 760 mmHg
• Flash Point: 62.3°C
• Density: 1.098g/cm³
• Vapor Pressure: 0.643mmHg at 25°C
• Refractive Index: 1.473
• CAS DataBase Reference: 1,3,5,5-tetramethylimidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5,5-tetramethylimidazolidine-2,4-dione(15414-89-8)
• EPA Substance Registry System: 1,3,5,5-tetramethylimidazolidine-2,4-dione(15414-89-8)

Safety Data

• Hazardous Substances Data: 15414-89-8(Hazardous Substances Data)

Upstream product

• 90832-46-5 2,2,3,5-tetramethylhydantoic acid 
• 2566-34-9 2-(methylamino)isobutyric acid 
• 186581-53-3 diazomethane 
• 90832-47-6 potassium-2,2,3,5-tetramethylhydantoate 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 74-88-4 methyl iodide 

Relevant articles and documents

DETERMINATION OF HYDANTOINS IN CONDENSATE WATER FROM LIGNITE GASIFICATION.

A method for the characterization of the nonsolvent extractable hydantoins in condensate water from the slagging fixed bed gasification of lignite was developed. The water was treated with activated carbon and the dydantoins were extracted from the carbon with boiling alcohol. A number of 5,5-dialkyl- and 5-alkylhydantoins were separated by gas chromatography on a polar fused silica capillary column and characterized by comparision of their mass spectra with known standards and by matching retention indexes. For compounds with low intensity molecular ions, chemical ionization with methane was used for identification. The 1,3-dimethyl derivatives of the hydantoins were prepared and chromatographed on a nonpolar capillary column to provide further confirmation of the presence of the hydantoins.

INTRAMOLECULAR NUCLEOPHILIC ATTACK ON CARBOXYLATE BY UREIDE ANION. GENERAL ACID-BASE CATALYSIS OF THE ALKALINE CYCLISATION OF 2,2,3,5-TETRAMETHYLHYDANTOIC ACID

The cyclisation of the title compound to the corresponding hydantoin is a model for the carboxylation of biotin by hydrogen carbonate.The reaction is rapid over the whole pH range, and is catalysed by both general acids and general bases.Above ph 9.2 the reaction is first order in hydroxide, which is shown to act as a general base.The prefered mechanism is specific base-general acid catalysis, involving nucleophilic attack by the ureide anion on the ionised carboxy group, assisted by proton transfer from the general acid.This defines also the mechanism of the reverse reaction, and clarifies for the first time the role of the second hydroxide ion in the ->2 term for the hydrolysis of amides with good leaving groups.