39565

1,3-Dimethylbarbituric acid

≥99.0% (T)

• Synonym(s): 1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
• Empirical Formula (Hill Notation): C₆H₈N₂O₃
• CAS Number: 769-42-6
• Molecular Weight: 156.14
• Beilstein/REAXYS Number: 139810
• EC Number: 212-211-7
• MDL number: MFCD00006675
• UNSPSC Code: 12352100
• PubChem Substance ID: 57649861
• NACRES: NA.22

Properties

• assay: ≥99.0% (T)
• form: solid
• ign. residue: ≤0.1%
• mp: 121-123 °C (lit.); 123-126 °C
• solubility: hot water: soluble 0.5 g/10 mL, clear, colorless to faintly yellow
• SMILES string: CN1C(=O)CC(=O)N(C)C1=O
• InChI: 1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3
• InChI key: VVSASNKOFCZVES-UHFFFAOYSA-N

Description

General description

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.

Application

1,3-Dimethylbarbituric acid may be 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.

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H302,H318
• pcodes: P264 - P270 - P280 - P301 + P312 - P305 + P351 + P338 - P501
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves