57270-81-2

Basic information

• Product Name: 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid
• Synonyms: 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid;5-(4-DIMETHYLAMINOBENZYLIDENE)1,3-DIMETHYLBARBITURIC ACID;1,3-Dimethyl-5-[4-(dimethylamino)benzylidene]barbituric acid;1,3-Dimethyl-5-[4-(dimethylamino)benzylidene]pyrimidine-2,4,6(1H,3H,5H)-trione;5-[[4-(Dimethylamino)phenyl]methylene]-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione;5-[4-(Dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione;Einecs 260-658-1
• CAS NO: 57270-81-2
• Molecular Formula: C₁₅H₁₇N₃O₃
• Molecular Weight: 287.31378
• EINECS: 260-658-1
• Mol File: 57270-81-2.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 437.8°Cat760mmHg
• Flash Point: 193.5°C
• Appearance: /
• Density: 1.283g/cm³
• Vapor Pressure: 7.25E-08mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid(57270-81-2)
• EPA Substance Registry System: 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid(57270-81-2)

Safety Data

• Hazardous Substances Data: 57270-81-2(Hazardous Substances Data)

Usage

Description

5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid is a complex chemical compound that belongs to the barbituric acid group. It features a barbituric acid core with a 4-(dimethylamino)phenyl group connected through a methylene linker, indicating potential biological activity, particularly in the central nervous system. Further research is required to ascertain its specific effects and applications.

Uses

Used in Pharmaceutical Industry:
5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid is used as a sedative or hypnotic agent for its potential to affect the central nervous system, providing calming or sleep-inducing effects. Its structure suggests it may have therapeutic applications in managing conditions related to anxiety, insomnia, or other disorders that could benefit from its sedative properties.
Used in Research and Development:
In the scientific community, 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid serves as a subject for research to explore its pharmacological properties, mechanism of action, and potential side effects. This could lead to the development of new drugs or therapies based on its chemical structure and activity.

InChI:InChI=1/C15H17N3O3/c1-16(2)11-7-5-10(6-8-11)9-12-13(19)17(3)15(21)18(4)14(12)20/h5-9H,1-4H3

Upstream product

• 24431-17-2 N-(p-dimethylaminobenzylidene)benzylamine 
• 57270-84-5 1,3-dimethyl-5-(4-methyl-benzylidene)-pyrimidine-2,4,6-trione 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 769-42-6 1,3-dimethylbarbituric acid 
• 889-37-2 N,N-dimethyl-4-((phenylimino)methyl)aniline 

Downstream Products

• 54459-73-3 5-benzylidene-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 1341225-24-8 7,9-dimethyl-4-(4-dimethylaminophenyl)-1,3-diphenyl-1,2,7,9-tetraaza-spiro[4.5]dec-2-ene-6,8,10-trione 
• 1259377-27-9 4-(6-(4-(dimethylamino)phenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,6-hexahydrofuro[2,3-d]pyrimidin-5-yl)benzonitrile 
• 1093169-06-2 3-(1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-3-(4-(dimethylamino)phenyl)-2-(4-nitrophenyl)propionitrile 

Relevant articles and documents

Merocyanine-type dyes from barbituric acid derivatives

The preparation and the solvatochromic behavior of two dyes, obtained by condensation of N,N′-dimethylbarbituric acid with dimethylaminobenzaldehyde and with 4,4′-bis(N,N-dimethylamino)benzophenone (Michler's ketone) are described. The latter dye is rathe

Barbituric acid based fluorogens: Synthesis, aggregation-induced emission, and protein fibril detection

Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced emission, are systematically characterized. Afterward, the structure-property relationships of these barbituric acid based fluorogens are discussed. Finally, we demonstrate their potential applications for protein amyloid fibril detection.

Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines

Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.