18015-04-8

Basic information

• Product Name: 5-(thiophen-2-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• Synonyms: 2,4,6(1H,3H,5H)-pyrimidinetrione, 5-(2-thienylmethylene)-; 5-(2-Thienylmethylene)pyrimidine-2,4,6(1H,3H,5H)-trione; 5-(2-thienylmethylidene)hexahydropyrimidine-2,4,6-trione
• CAS NO: 18015-04-8
• Molecular Formula: C₉H₆N₂O₃S
• Molecular Weight: 222.2205
• Mol File: 18015-04-8.mol
• Article Data: 10

Chemical Properties

• Density: 1.529g/cm³
• Refractive Index: 1.674
• CAS DataBase Reference: 5-(thiophen-2-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(thiophen-2-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione(18015-04-8)
• EPA Substance Registry System: 5-(thiophen-2-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione(18015-04-8)

Safety Data

• Hazardous Substances Data: 18015-04-8(Hazardous Substances Data)

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 873-83-6 4-Amino-2,6-dihydroxypyrimidine 
• 1753-47-5 5-(4-dimethylaminobenzylidene)barbituric acid 
• 131196-45-7 N-[(1E)-thiophen-2-ylmethylidene]benzenemethanamine 
• 28162-32-5 2-(2-thienyl)-1-cyanoacrylonitrile 
• 67-52-7 BARBITURIC ACID 

Downstream Products

• 1001318-07-5 3-(2-thienyl)-2-phenyl-3,3a-dihydro-2H-pyrazolo[3,4-d]pyrimidine-4,6-(5H,7H)-dione 
• 98-03-3 thiophene-2-carbaldehyde 
• 1753-47-5 5-(4-dimethylaminobenzylidene)barbituric acid 
• 131196-45-7 N-[(1E)-thiophen-2-ylmethylidene]benzenemethanamine 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 3878-18-0 2-(2-thienyl)-1H-benzimidazole 

Relevant articles and documents

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Barbituric acid in the synthesis of fused 1,7-phenanthroline derivatives

New 7-aryl(hetaryl)-7,8,9,10,11,12-hexahydropyrimido[5,4-b][1,7] phenanthroline-9,11-diones have been synthesized by three-component condensation of barbituric acid with quinolin-5-amine and aromatic or heteroaromatic aldehydes.

Synthesis of fused uracils: Pyrano[2,3-d]pyrimidines and 1,4-bis(pyrano[2,3-d]pyrimidinyl)benzenes by domino Knoevenagel/Diels-Alder reactions

Knoevenagel condensation of barbituric acids with aromatic aldehydes containing one or two formyl groups was carried out. 5-Arylidenebarbituric acids underwent smooth hetero-Diels-Alder (HDA) reactions with enol ethers to afford cis and trans diastereoisomers of pyr-ano[2,3-d]pyrimidine-2,4-diones and 5,5′-(1,4-phenylene)-bis[2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione] derivatives in excellent yields (75-88%). Syntheses were realized by Knoevenagel condensation and HDA reaction in four different reaction conditions: Knoevenagel condensation in water and Diels-Alder reaction in methylene chloride solution, Knoevenagel condensation in water and Diels-Alder reaction without solvent, three-component one-pot reaction in methylene chloride solution, or three-component one-pot reaction in water. All reactions were carried out without catalyst at room temperature. The reactions of malononitrile with Knoevenagel condensation products of barbituric acids and heteroaromatic aldehydes or terephthalaldehyde were examined and did not provide corresponding pyranopyrimidines.