7391-66-4

Basic information

• Product Name: 1,3-Dimethyl-5-phenylbarbituric acid
• Synonyms: (5-PHENYL-1,3-DIMETHYL)BARBITURIC ACID;1,3-DIMETHYL-5-PHENYL-2,4,6(1H,3H,5H)-PYRIMIDINETRIONE;1,3-dimethyl-5-phenylbarbituric acid;1,3-Dimethyl-5-phenyl-pyrimidine-2,4,6-trione;AURORA KA-3845;1,3-dimethyl-5-phenyl-barbituricaci;5-Phenyl-1,3-dimethyl-barbituricadid(PDMBA);5-PHENYL-1,3-DIMETHYL-BARBITURIC ACID 99%
• CAS NO: 7391-66-4
• Molecular Formula: C₁₂H₁₂N₂O₃
• Molecular Weight: 232.24
• EINECS: 230-981-2
• Product Categories: Organic acids
• Mol File: 7391-66-4.mol

Chemical Properties

• Melting Point: 140.0-140.5 °C
• Boiling Point: 352.7°Cat760mmHg
• Flash Point: 155.2°C
• Appearance: /
• Density: 1.274g/cm³
• Vapor Pressure: 3.78E-05mmHg at 25°C
• Refractive Index: 1.57
• PKA: 4.41±0.20(Predicted)
• CAS DataBase Reference: 1,3-Dimethyl-5-phenylbarbituric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-5-phenylbarbituric acid(7391-66-4)
• EPA Substance Registry System: 1,3-Dimethyl-5-phenylbarbituric acid(7391-66-4)

Safety Data

• Hazardous Substances Data: 7391-66-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dimethyl-5-phenylbarbituric acid is used as a sedative and hypnotic medication for the treatment of conditions such as insomnia, anxiety, and epilepsy. Its mechanism of action involves the enhancement of GABA activity, which results in calming and sleep-inducing effects.
However, due to the risks of tolerance, dependence, and withdrawal symptoms associated with its use, the popularity of 1,3-Dimethyl-5-phenylbarbituric acid has diminished in favor of newer, safer sedative-hypnotic drugs. Despite this, it may still be utilized in specific clinical situations where its particular pharmacological profile is deemed necessary.

InChI:InChI=1/C12H12N2O3/c1-13-10(15)9(8-6-4-3-5-7-8)11(16)14(2)12(13)17/h3-7,9H,1-2H3

Upstream product

• 96-31-1 N,N'-Dimethylurea 
• 2613-89-0 phenylmalonic acid 
• 74808-90-5 5-diazo-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 71-43-2 benzene 
• 769-42-6 1,3-dimethylbarbituric acid 
• 591-50-4 iodobenzene 
• 83-13-6 diethyl 2-phenylmalonate 
• 108-86-1 bromobenzene 

Downstream Products

• 21870-33-7 5-(4-benzo[1,3]dithiol-2-ylidene-cyclohexa-2,5-dienylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 83609-86-3 5-Benzyl-1,3-dimethyl-5-phenyl-pyrimidin-2,4,6(1H,3H,5H)-trion 
• 5841-66-7 3-Methyl-5-phenyl-oxazol-2,4(3H,5H)-dion 
• 103929-62-0 5-hydroxy-1,3-dimethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 569337-38-8 5-bromo-1,3-dimethyl-5-phenylbarbituric acid 
• 1439383-38-6 1,3',5-trimethyl-2'-phenylspiro[1,5-diazinane-3,1'-indene]-2,4,6-trione 
• 51759-18-3 6-chloro-1,3-dimethyl-5-phenyl-pyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center

An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed. The rearrangement reactions use fac-Ir(ppy)3, visible light and commercially available fluoroalkyl halides and can generate valuable multisubstituted perfluoroalkylated compounds in a single step that would be challenging to prepare by other methods. Mechanistically, the photoinduced alkyl radical addition to an alkene leads to the migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center with the concomitant generation of a C-radical bearing two electron-withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence.

PHOTOLABILE BARBITURATE COMPOUNDS

The present disclosure provides a redox initiator system for initiating polymerization comprising an oxidizing agent, a photolabile reducing agent derived from a barbiturate, and a transition metal complex that participates in a redox cycle. On exposure to actinic radiation, such as UV, the photolabile compound photolyzes, releasing the reducing agent and initiating the redox-initiated polymerization.

Method for synthesizing 5-substituted barbituric acid derivative under catalysis of rare earth chloride

The invention belongs to the technical field of synthetic chemistry, and particularly relates to a method for synthesizing a 5-substituted barbituric acid derivative under the catalysis of a rare earth chloride. The preparation method comprises: dissolving a halogenated hydrocarbon and 1,3-dimethyl barbituric acid in an organic solvent, carrying out a reaction for 6-10 h at a room temperature by using a rare earth chloride as a catalyst, and separating and purifying to obtain the 5-substituted barbituric acid derivative. According to the invention, the method has characteristics of simple andenvironmentally-friendly synthesis process, excellent selectivity, high yield and wide substrate range, and further has wide application value in the fields of biology, pharmaceutical chemistry industry and the like.

Method for greenly synthesizing 5-hydroxy-5-alkyl disubstituted barbituric acid derivative by amine catalysis of air oxidation

The invention relates to the field of oxidative synthesis, and in particular, relates to a 5-hydroxy-5-alkyl disubstituted barbituric acid derivative greenly synthesized by amine catalysis of air oxidation and a method thereof. The amine-catalyzed oxidation reaction of a 5-substituted 1,3-dimethylbarbituric acid derivative is studied; reaction catalysts and solvents are screened, hydroxylation ofalpha-C-H of 5-aryl or benzyl substituted barbituric acid compounds is found out to be realized through catalytic reaction under different conditions. The method has the following characteristics: (1)air is used as the source of hydroxyl functional groups, so the requirements of green development are met; (2) easily available and cheap alkali R3N rather than expensive metal catalysts is used; and(3) stoichiometric harmful phosphine compounds are prevented from being used as additives and reductants.

Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds

A commercially available rhodium(II) complex catalyzes the direct arylation of 5-diazobarbituric acids with arenes, allowing straightforward access to 5-aryl barbituric acids. Free N-H groups are tolerated on the barbituric acid, with no complications arising from N-H insertion processes. This method was applied to the concise synthesis of a potent matrix metalloproteinase (MMP) inhibitor.

Functionalization of Csp3-H and Csp 2-H bonds: Synthesis of spiroindenes by enolate-directed ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl-1,3-dicarbonyl compounds

Ru(de) awakening: The synthesis of carbocycles by the ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl cyclic 1,3-dicarbonyl substrates is described. Proceeding by the functionalization of C sp 3-H and C sp 2-H bonds, and the formation of an all-carbon quaternary center, the reaction provides a diverse range of spiroindenes in good yields with high levels of regioselectivity. Copyright

4-Aminouracils and Pyrimidoindolediones from 4-Azidouracils

Azidouracils (3), which are obtained from barbituric acids (1), can easily be cyclized to pyrimidoindoles (4) or converted into 4-aminouracils (6). - Keywords: 4-Azidouracil; 1H-Pyrimidoindole-2,4(3H,9H)-dione; 4-Aminouracil; 4-Phosphoranylideneaminouracil; Cyclodehydrogenation; Thermolysis