32282-45-4

Basic information

• Product Name: 1-(1,3-dimethyl-2,5-dioxoimidazolidin-4-yl)urea
• CAS NO: 32282-45-4
• Molecular Formula: C₆H₁₀N₄O₃
• Molecular Weight: 186.1686
• Mol File: 32282-45-4.mol
• Article Data: 4

Chemical Properties

• Density: 1.47g/cm³
• Refractive Index: 1.599
• CAS DataBase Reference: 1-(1,3-dimethyl-2,5-dioxoimidazolidin-4-yl)urea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1,3-dimethyl-2,5-dioxoimidazolidin-4-yl)urea(32282-45-4)
• EPA Substance Registry System: 1-(1,3-dimethyl-2,5-dioxoimidazolidin-4-yl)urea(32282-45-4)

Safety Data

• Hazardous Substances Data: 32282-45-4(Hazardous Substances Data)

Upstream product

• 944-73-0 1,3-dimethyluric acid 
• 19039-41-9 7,9-dimethyluric acid 
• 160486-41-9 5-isopropoxy-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 
• 106887-63-2 5-methoxy-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 
• 106887-61-0 5-chloro-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 

Downstream Products

• 57-13-6 urea 

Relevant articles and documents

Conformational and Stereoelectronic Control in Ring-Transformations of cis-4,5-Dialkoxytetrahydropurine-2,6,8-triones

Divergent acid-catalysed ring-openings of 4,5-dimethoxytetrahydropurine-2,6,8-triones 2 at position 4, yielding 1-(5-methoxyhydantoin-5-carbonyl)ureas 4 (R7 = Me) or 5-methoxy-5-ureido-2,4,6-pyrimidinetriones 5 (R7 = H), can be rationalized by assuming a preference for one of two conformational isomers of the cis-fused system, associated with the N-substitution effects. Intramolecular transamidation 5→4 presumably occurs via a bicyclic acid aminal type intermediate 3, heretofore misassigned as the reaction product. A curious base-catalysed rearrangement was encountered with the 5 (R1 = R3 = Me, R7 = H) cases, which afforded 5-methoxy-1,5-bis(methylaminocarbonyl)hydantoins 7. Remarkable stability of the conformationally rigid propellane type 4,5-ethylenedioxytetrahydropurine-2,6,8-triones 9 toward acids, shows that the mode of zing-opening at position 4 is controlled by powerful stereoelectronic factors. However, an alternative ring-opening at the 1,6-bond has occurred on heating aqueous solutions of 9a (R7 = H); the ensuing decarboxylative rearrangement leads to 1,3-dimethylallantoin (12) and its precursor, 1-(2-hydroxyethoxy)-2,4-dimethyl-3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0] octane(11).

Comparison of electrochemical and enzymic oxidation of 7,9-dimethyluric acid

The oxidation of 7,9-dimethyluric acid has been studied in aqueous phosphate buffers in the pH range 2.3-10.0 at a variety of solid electrodes. The conjugate base is found as the electroactive species which on 2e, H+ oxidation gives an unstable diimine. The attack of water molecule on the diimine in a follow up chemical reaction gives a UV-absorbing intermediate which decomposes in a pseudo-first order reaction to give alloxan and 1,3-dimethylurea at pH 3.0 and 1,3-dimethylallantoin and 1,3-dimethyl-5-hydroxyhydantoin-5-carboxamide at pH 7.2. The electrochemical behaviour of dimethyluric acid at PGE, GCE and Ft electrodes is the same. A comparison of electrochemical behaviour with unsubstituted uric acid indicates that methyl groups at positions 7 and 9 shift the Ep towards less positive potential. However, the overall course of electrode reaction remains unchanged. The peroxidase catalysed oxidation of 7,9-dimethyluric acid also exhibites the same spectral and kinetic behaviour and hence it is concluded that electrochemical and enzymic oxidation proceed by an identical EC mechanism.