1,3-Dimethylbarbituric acid

Base Information

• Chemical Name: 1,3-Dimethylbarbituric acid
• CAS No.: 769-42-6
• Deprecated CAS: 213833-88-6,41949-07-9,342615-73-0,863970-57-4,936361-69-2,952003-94-0,959586-34-6,1030585-39-7,1188497-83-7,1240326-21-9,1392010-45-5,1429128-12-0,1030585-39-7,1188497-83-7,1240326-21-9,1392010-45-5,342615-73-0,41949-07-9,863970-57-4,936361-69-2,952003-94-0,959586-34-6
• Molecular Formula: C6H8N2O3
• Molecular Weight: 156.141
• Hs Code.: 29339900
• European Community (EC) Number: 212-211-7
• NSC Number: 61918
• DSSTox Substance ID: DTXSID0061115
• Nikkaji Number: J135.896K
• Wikidata: Q72469355
• Mol file: 769-42-6.mol

Synonyms:1,3-dimethylbarbituric acid

Chemical Property of 1,3-Dimethylbarbituric acid

Chemical Property:

• Appearance/Colour: Yellow or brownish powder
• Vapor Pressure: 0.0746mmHg at 25°C
• Melting Point: 121-123 °C(lit.)
• Refractive Index: 1.511
• Boiling Point: 228.1 °C at 760 mmHg
• PKA: pK1:4.68(+1) (25°C)
• Flash Point: 95.3 °C
• PSA: 57.69000
• Density: 1.322 g/cm³
• LogP: -0.69730
• Storage Temp.: -20°C Freezer
• Solubility.: hot water: soluble0.5g/10 mL, clear, colorless to faintly yellow
• Water Solubility.: Soluble in water.
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 156.05349212
• Heavy Atom Count: 11
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dimethylbarbituric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C(=O)CC(=O)N(C1=O)C
• Uses: 1,3-Dimethylbarbituric acid is used as a catalyst in the Knoevenagel condensation of a series of aromatic aldehydes. It is also used in the synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives and enantioselective synthesis of isochromene pyrimidinedione derivatives. 1,3-Dimethyl Barbituric Acid (Urapidil Impurity 4) is a derivative of Barbituric acid. All of the barbituric acid derivatives which have been reported to have pronounced hypnotic activity are disubstituted in the 5-position.

Technology Process of 1,3-Dimethylbarbituric acid

There total 52 articles about 1,3-Dimethylbarbituric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

5,5-dibromo-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione (56983-59-6) + phenol (108-95-2,27073-41-2) → 1,3-dimethylbarbituric acid (769-42-6) + 4-bromo-phenol (106-41-2)

Guidance literature:

at 100 ℃; for 48h;

DOI:10.1016/j.tet.2009.10.049

Reference yield: 90.0%

6-methoxy-1,3-dimethyluracil (4097-20-5) → 1,3-dimethylbarbituric acid (769-42-6)

Guidance literature:

With hydrogenchloride; In ethanol; for 0.833333h; Heating;

Reference yield: 85.0%

N,N'-Dimethylurea (96-31-1) + malonic acid (141-82-2) → 1,3-dimethylbarbituric acid (769-42-6)

Guidance literature:

In acetic anhydride;

DOI:10.1134/S1070428019060174

upstream raw materials:

BARBITURIC ACID

dimethyl sulfate

6-Amino-1,3-dimethylbarbituric acid

1,1-Dimethylurea

Downstream raw materials:

5-(benzo[d][1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

1,3-dimethyl-7-phenyl-1,5,6,7-tetrahydro-pyrano[2,3-d]pyrimidine-2,4-dione

1,3-dimethyl-7-(2-oxo-1,4-diphenyl-1,2-dihydro-pyrrol-3-ylidene)-1,7-dihydro-pyrano[2,3-d]pyrimidine-2,4-dione

5-[3-(2-hydroxy-phenyl)-3-oxo-1-(4-oxo-4H-chromen-3-yl)-propyl]-1,3-dimethyl-pyrimidine-2,4,6-trione

Refernces

• 1、 Shukla,Bishnoi,Devi,Kumar,Srivastava,Srivastava,Fatma. "Synthesis, Characterization, and in vitro Antibacterial Evaluation of Barbituric Acid Derivatives". . p. 860 - 865. Retrieved 2019.
• 2、 Gu, Ruirui,Flidrova, Karolina,Lehn, Jean-Marie. "Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines". supporting information. p. 5560 - 5568. Retrieved 2018/05/01.