21544-73-0

Basic information

• Product Name: 5,5-dichloro-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• CAS NO: 21544-73-0
• Molecular Formula: C₆H₆Cl₂N₂O₃
• Molecular Weight: 225.0294
• Mol File: 21544-73-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 265.4°C at 760 mmHg
• Flash Point: 114.3°C
• Density: 1.63g/cm³
• Vapor Pressure: 0.00916mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 5,5-dichloro-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dichloro-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(21544-73-0)
• EPA Substance Registry System: 5,5-dichloro-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(21544-73-0)

Safety Data

• Hazardous Substances Data: 21544-73-0(Hazardous Substances Data)

Upstream product

• 5417-13-0 1,3-dimethylvioluric acid 
• 769-42-6 1,3-dimethylbarbituric acid 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 10026-13-8 phosphorus pentachloride 
• 2835-45-2 amalic acid 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 30066-93-4 5-amino-1,3-dimethyl-pyrimidine-2,4,6-(1H,3H,5H)-trione 
• 30537-82-7 betaine of 1,3-dimethyl-5-phenyliodoniobarbituric acid 
• 58378-09-9 1,3,1',3'-tetramethylhydurilic acid 
• 74808-90-5 5-diazo-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 

Downstream Products

• 769-42-6 1,3-dimethylbarbituric acid 
• 2757-85-9 1,3-dimethylalloxan 
• 21991-30-0 5,5-dibenzyl-1,3-dimethyl-2,3,4(1H,3H,5H)pyrimidinetrione 
• 15018-52-7 5-benzyl-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 14305-99-8 1,3-dimethyl-5-nitro-pyrimidin-2,4,6(1H,3H,5H)-trione 
• 5417-13-0 1,3-dimethylvioluric acid 

Relevant articles and documents

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Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives - New synthetic routes and crystal structures

We describe simple, convenient and high-yielding nucleophilic substitution reactions to synthesize new derivatives of 1,3-dimethylbarbituric acid (1a). Based on its active C5 position, condensing 1a with sulfuryl chloride gives the corresponding 5,5-dichloro-1,3-dimethylbarbituric acid (13). The latter was reacted with silver nitrite and potassium cyanide to afford 5-chloro-5-nitro-1, 3-dimethylbarbituric acid (14) and 5-cyano-1,3-dimethylbarbiturate (17), respectively. Furthermore, by employing the nucleophilic character of 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (8) the obtained compounds 13 and 14 have been converted to 2-chloro-1,3-diisopropyl-4,5- dimethyl-1H-imidazol-3-ium-1,3-dimethyl-5-nitro-1,3-dimethylbarbiturate (18) and 1,3-dimethylbarbituric acid trimer (21), respectively. X-ray structures for compounds 13, 14, 17, 18 and 21 were determined.

Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene

Pre-formed phenyliodonium ylides of cyclic and acyclic β-diketones, β-keto esters and β-diesters were reacted with (dichloroiodo)benzene, resulting in transfer of both chloride ligands onto the ylidic carbon. These two hypervalent iodine(III) compounds exhibit high reactivity towards each other under mild reaction conditions and typically afford the gem-dichloride products in good yield. Upon comparison of these chlorination reactions with those of the analogous diazocarbonyl compounds, reactions of iodonium ylides were unilaterally faster, and often gave the products in higher yield.

Dichlorination of α-Diazo-β-dicarbonyls using (dichloroiodo)benzene

Abstract α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleo-philicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.