89356-38-7

Basic information

• Product Name: Pyrrolo[3,4-d]imidazole-2,4-dione, 6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethyl-, cis-
• CAS NO: 89356-38-7
• Molecular Formula: C7H10N4O3
• Molecular Weight: 198.181
• Mol File: 89356-38-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Pyrrolo[3,4-d]imidazole-2,4-dione, 6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethyl-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[3,4-d]imidazole-2,4-dione, 6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethyl-, cis-(89356-38-7)
• EPA Substance Registry System: Pyrrolo[3,4-d]imidazole-2,4-dione, 6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethyl-, cis-(89356-38-7)

Safety Data

• Hazardous Substances Data: 89356-38-7(Hazardous Substances Data)

Upstream product

• 151-50-8 potassium cyanide 
• 135636-66-7 butane-2,3-dione mono-oxime 

Relevant articles and documents

Application of the Bucherer Hydantoin Synthesis to Diacetyl Mono-oxime. The Mechanism of the Bucherer Reaction, and the Constitution of the Hypothetical 'Dimethylbishydantoin' of Bucherer and Lieb

The major product obtained when the Bucherer conditions for hydantoin synthesis were applied to diacetyl mono-oxime was (3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrroloimidazole-2,4-dione (3).Two minor products (7) and (9) are related to (3) but a third, the imidazole 1-oxide (10), is not.Compound (10) was obtained from diacetyl mono-oxime and ammonium carbonate in the absence of cyanide.It is proposed that 4,4-disubstituted 5-imino-oxazolidin-2-ones (18), postulated by Bucherer and Steiner to be intermediates in hydantoin syntheses, rearrange to hydantoins by a base catalysed E1cB mechanism.It is further proposed that (3) is the hypothetical 'dimethylbishydantoin' (35) reported by Bucherer and Lieb in 1934.