57270-80-1

Basic information

• Product Name: 5-[(4-hydroxyphenyl)methylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• Synonyms: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-[(4-hydroxyphenyl)methylene]-1,3-dimethyl-; 5-(4-Hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• CAS NO: 57270-80-1
• Molecular Formula: C₁₃H₁₂N₂O₄
• Molecular Weight: 260.2454
• Mol File: 57270-80-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 418.8°C at 760 mmHg
• Flash Point: 207.1°C
• Density: 1.412g/cm³
• Vapor Pressure: 1.31E-07mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 5-[(4-hydroxyphenyl)methylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(4-hydroxyphenyl)methylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(57270-80-1)
• EPA Substance Registry System: 5-[(4-hydroxyphenyl)methylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(57270-80-1)

Safety Data

• Hazardous Substances Data: 57270-80-1(Hazardous Substances Data)

Upstream product

• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 769-42-6 1,3-dimethylbarbituric acid 

Downstream Products

• 110449-08-6 5-(4'-acetoxybenzylidene)-1,3-dimethylbarbituric acid 

Relevant articles and documents

Application of bioorthogonal hetero-Diels-Alder cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid and vinyl thioether for imaging inside living cells

New bioorthogonal cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid as 1-oxa-1,3-butadienes and vinyl thioether as a dienophile has been applied to imaging inside living cells. The reaction is high yielding, selective, and fast in aqueous media. The proposed 1-oxa-1,3-butadiene derivative conjugated to a FITC fluorochrome selectively and rapidly labels the cancer cells pretreated with the dienophile-taxol. The second order rate constants k2 for various proposed bioorthogonal cycloadditions were estimated to be in the range from 0.9 × 10-2 M-1 s-1 to 1.4 M-1 s-1, which is much better than in the case of the first generation TQ-ligation (o-quinolinone quinone methide and vinyl thioether ligation, k2 = 1.5 × 10-3 M-1 s-1) and comparable or better to that for the second generation TQ-ligation (k2 = 2.8 × 10-2 M-1 s-1). The reaction rate constants k2 of proposed ligation reactions are in the range of the rate constants k2 for tetrazines and norbornenes or tetrazines and cyclopropenes. These findings indicate that this chemistry is suitable for in vitro imaging experiments.

Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles

The study is devoted to one-pot reaction of 1,3-dimethylbarbituric acid with aromatic aldehydes and ammonium acetate using Fe3O4 nanoparticles as efficient and magnetically recyclable catalysts. Aromatic aldehydes substituted with electron-withdrawing groups or none, reacted successfully with 1,3-dimethylbarbituric acid and ammonium acetate to give new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidine derivatives (can be also named as pyrido[2,3-d:6,5-d′]dipyrimidines) in high yields over relatively short reaction time. The Knoevenagel condensation products were isolated using aromatic aldehydes bearing electron-donating substituents. The catalyst could be efficiently used for four times without substantial reduction in its activity. The new products were characterized on the basis of FT-IR, 1H NMR and 13C NMR spectral data.

Effect of reaction parameters on the synthesis of 5-arylidene barbituric acid derivatives in ball mills

The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (νrot), milling ball diameter (dMB), milling ball filling degree (φMB), and beaker size