7526-77-4

Basic information

• Product Name: 5-(propan-2-ylidene)imidazolidine-2,4-dione
• Synonyms: 2,4-imidazolidinedione, 5-(1-methylethylidene)-
• CAS NO: 7526-77-4
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.1399
• Mol File: 7526-77-4.mol
• Article Data: 5

Chemical Properties

• Density: 1.211g/cm³
• Refractive Index: 1.504
• CAS DataBase Reference: 5-(propan-2-ylidene)imidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(propan-2-ylidene)imidazolidine-2,4-dione(7526-77-4)
• EPA Substance Registry System: 5-(propan-2-ylidene)imidazolidine-2,4-dione(7526-77-4)

Safety Data

• Hazardous Substances Data: 7526-77-4(Hazardous Substances Data)

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 67-64-1 acetone 
• 91121-79-8 5-isopropylidene-2-thioxo-imidazolidin-4-one 
• 857768-07-1 4-isopropylidene-5-thioxo-imidazolidin-2-one 
• 69630-85-9 5-(α-mercapto-isopropyl)-imidazolidine-2,4-dione 
• 77210-10-7 (S)-(+)-5-(1-mercapto-1-methyl)ethylhydantoin 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 77176-17-1 (S)-3-Mercapto-3-methyl-2-ureido-butyric acid 
• 56-40-6 glycine 
• 52-67-5 3,3-dimethyl-D-cysteine 
• 759-05-7 3-methyl-2-ketobutanoic acid 
• 17356-08-0 thiourea 

Downstream Products

• 16935-34-5 5-isopropyl-imidazolidine-2,4-dione 
• 15784-52-8 Potassium; 3-methyl-2-oxo-butyrate 
• 3715-29-5 sodium 3-methyl-2-oxobutyrate 
• 54905-59-8 D-5-isopropylhydantoin 
• 40856-74-4 (5S)-5-(propan-2-yl)imidazolidine-2,4-dione 

Relevant articles and documents

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

Process for production of hydantoin derivatives

Hydantoin derivatives are industrially advantageously produced at a high yield by reacting hydantoin with carbonyl compounds in the presence of (i) amino acids or the salts thereof and (ii) inorganic alkali compounds for a relatively short reaction time in an aqueous medium.

5-Secondary alkylidene hydantoins

A 5-Secondary alkylidene hydantoin having the formula STR1 in which: (a) R is an alkyl group having 1-2 carbon atoms; and (b) X is hydrogen or a phenyl group can be prepared by condensing a hydantoin having the formula STR2 and a ketone having the formula STR3 in the presence of ammonia or an amine catalyst, the amine being a primary amine having a pKb between about 3 and about 5.