3237-50-1

Basic information

• Product Name: 5,5-dihydroxyperhydropyrimidinetrione
• Synonyms: 5,5-dihydroxyperhydropyrimidinetrione;5,5-Dihydroxy-2,4,6(1H,3H,5H)-pyrimidinetrione;5,5-Dihydroxybarbituric acid;5,5-Dihydroxyhexahydropyrimidine-2,4,6-trione;5,5-Dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione;5,5-dihydroxy-1,3-diazinane-2,4,6-trione
• CAS NO: 3237-50-1
• Molecular Formula: C₄H₄N₂O₅
• Molecular Weight: 160.08496
• EINECS: 221-796-8
• Mol File: 3237-50-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 285.94°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.8517 (rough estimate)
• Refractive Index: 1.4610 (estimate)
• PKA: 6.60±0.10(Predicted)
• CAS DataBase Reference: 5,5-dihydroxyperhydropyrimidinetrione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dihydroxyperhydropyrimidinetrione(3237-50-1)
• EPA Substance Registry System: 5,5-dihydroxyperhydropyrimidinetrione(3237-50-1)

Safety Data

• Hazardous Substances Data: 3237-50-1(Hazardous Substances Data)

Usage

General Description

Triclinic piacoidal crystals. White granular solid.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Organic imides, of which alloxan is one, react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generate mixed oxides of nitrogen.

Fire Hazard

Flash point data for 5,5-dihydroxyperhydropyrimidinetrione are not available. 5,5-dihydroxyperhydropyrimidinetrione is probably combustible.

InChI:InChI=1/C4H4N2O5/c7-1-4(10,11)2(8)6-3(9)5-1/h10-11H,(H2,5,6,7,8,9)

Upstream product

• 69-93-2 uric Acid 
• 67-52-7 BARBITURIC ACID 
• 51-20-7 5-bromouracil 
• 653-63-4 2'-deoxyadenosine-5'-monophosphoric acid 
• 66-22-8 uracil 
• 73636-25-6 C₁₃H₁₃N₂O⁽¹⁺⁾*C₄H₂N₂O₄^(1-) 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 

Downstream Products

• 109015-67-0 5-[2-(4-bromo-phenyl)-1-methyl-2-oxo-ethyl]-5-hydroxy-barbituric acid 
• 112271-16-6 5-hydroxy-5-[4-phenyl-2-(1-phenyl-ethylLiDenehydrazino)-thiazol-5-yl]-barbituric acid 
• 6960-27-6 alloxan thiosemicarbazone 
• 7472-19-7 5-benzylmercapto-5-hydroxy-barbituric acid 
• 21914-07-8 5,5-diphenylbarbituric acid 
• 585-05-7 oxaluric acid 

Relevant articles and documents

The crystal structure of 5,5-dihydroxybarbituric acid trihydrate.

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Facile synthesis of 1,2,3-tricarbonyls from 1,3-dicarbonyls mediated by cerium(IV) ammonium nitrate

A mild and efficient protocol for the synthesis of vicinal tricarbonyl compounds from β-dicarbonyls in a single step using cerium(IV) ammonium nitrate as a catalytic oxidant is described. Ease of execution, wide substrate scope and the suitability for the synthesis of commercially important compounds like ninhydrin, alloxan and oxoline make this reaction particularly noteworthy.

Reduction of Vicinal Tricarbonyl Compounds by Reduced Nicotinamide Adenine Dinucleotide Model and Electron-Transport Systems

The reduction of vicinal tricarbonyl compounds such as alloxan (A) and ninhydrin (NY) with 1-benzyl-1,4-dihydronicotinamide (BNAH; NADH model) was investigated.In the reduction of A with BNAH, the radical anion (A-.Py+) of A as the 1-benzyl-3-carbamoylpyridinium salt and the dialuric acid (D) was obtained by one-electron and two-electron reduction,respectively.Similarly,hydrindantin (HDT) and 2-hydroxy-1,3-indandione (HID) were also afforded in the reduction of NY with BNAH.Further,the reductions of alloxantin (AT) and HDT with BNAH were performed to give D and HID,respectively.The reduction of lipoic acid (LA) and viologens (V2+) with BNAH, which could not be reduced without A or NY, proceeded smoothly in their presence,and they proved to be useful as mediators for catalytic reduction of LA and V2+.