1,3-Dimethylbarbituric acid - ≥99% , CAS No.769-42-6

CAS: 769-42-6 Cat. No.: D106283 Molecular Weight: 156.14 Beilstein Registry Number: 139810 EC Number: 212-211-7

GRADE & PURITY ≥99%

Synonyms

1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione | 1,3-dimethyl-1,3-diazinane-2,4,6-trione | N,N'-Dimethylbarbituric acid

Storage

Room temperature

Shipped In

Normal

Overview

1,3-Dimethylbarbituric acid (1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione) is an active methylene compound. It undergoes hollow Pd6 water-soluble cage, [{(tmen)Pd}6(timb)4](NO3)12 (tmen= N,N,N′,N′-tetramethylethylenediamine, timb=1,3,5-tris(1-imidazolyl)benzene)-catalyzed Knoevenagel condensation reaction with pyrene-1-carboxaldehyde.It undergoes self-sorted Pd7 molecular boat having an internal nanocavity (catalyst)-assisted Knoevenagel condensation reaction with various aromatic aldehydes. It has been synthesized by reacting 1,3-dimethylurea, malonic acid and acetic anhydride in acetic acid. It is widely used for the synthesis of various synthetic intermediates and heterocyclic compounds
Usually used in the following studies: Enantioselective synthesis of isochromene pyrimidinedione derivatives having five stereocenters, via one-pot Michael-Knoevenagel condensation-inverse-electron-demand hetero-Diels-Alder reaction;Synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives; Microwave promoted indirect functionalization of alcohols, via spirocyclisation employing a sequential one-pot Ir(III)/Pd(0) catalyzed process.

Specifications

Synonyms

1, 3-dimethylpyrimidine-2, 4, 6(1H, 3H, 5H)-trione | 1, 3-dimethyl-1, 3-diazinane-2, 4, 6-trione | N, N'-Dimethylbarbituric acid

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488184418
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488184418
• Canonical Smiles: CN1C(=O)CC(=O)N(C1=O)C
• IUPAC Name: 1,3-dimethyl-1,3-diazinane-2,4,6-trione
• InChIKey: VVSASNKOFCZVES-UHFFFAOYSA-N
• INCHI: 1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3
• Isomeric SMILES: CN1C(=O)CC(=O)N(C1=O)C
• WGK Germany: 3
• Molecular Weight: 156.14
• Beilstein: 139810
• Reaxy-Rn: 139810
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=139810&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives
        • Level5 Pyrimidones
          • Level6 Barbituric acid derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Pyrimidones
• Direct Parent: Barbituric acid derivatives
• Alternative Parents: N-acyl ureas Diazinanes 1,3-dicarbonyl compounds Dicarboximides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Barbiturate - N-acyl urea - Ureide - 1,3-diazinane - 1,3-dicarbonyl compound - Dicarboximide - Carbonic acid derivative - Urea - Carboxylic acid derivative - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organic nitrogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: hot water: soluble 0.5 g/10 mL, clear, colorless to faintly yellow
• Melt Point(°C): 121-123°C
• Molecular Weight: 156.140 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 156.053 Da
• Monoisotopic Mass: 156.053 Da
• Topological Polar Surface Area: 57.700 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 214.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chaoyue Xiong, Guodong Xue, Lijun Mao, Lianghong Gu, Chao He, Yonghao Zheng, Dongsheng Wang.  (2021)  Carbon Spacer Strategy: Control the Photoswitching Behavior of Donor–Acceptor Stenhouse Adducts.  LANGMUIR,      [PMID:33406356] [10.1021/acs.langmuir.0c03133]

2. Islam K Boshra, Guo Lin, Ahmed Elbeih.  (2020)  Influence of different crosslinking mixtures on the mechanical properties of composite solid rocket propellants based on HTPB.  HIGH PERFORMANCE POLYMERS,      [PMID:] [10.1177/0954008320940359]

3. Kai Li, Run-Hui Yu, Cheng-Mei Shi, Fu-Rong Tao, Tian-Duo Li, Yue-Zhi Cui.  (2018)  Electrospun nanofibrous membrane based on AIE-active compound for detecting picric acid in aqueous solution.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2018.02.032]

4. Kai Li, Yang Zhang, Bing Qiao, Furong Tao, Tianduo Li, Yunqiao Ding, Françisco M. Raymo, Yuezhi Cui.  (2017)  Facile fabrication of AIE/AIEE-active fluorescent nanoparticles based on barbituric for cell imaging applications.  RSC Advances,  7  (48): (30229-30241).  [PMID:] [10.1039/C7RA03956E]