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39565 Aldrich

1,3-Dimethylbarbituric acid

≥99.0% (T)

Synonym: 1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione

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Properties

Related Categories Building Blocks, C6 to C8, Chemical Synthesis, Heterocyclic Building Blocks, Pyrimidines More...
InChI Key   VVSASNKOFCZVES-UHFFFAOYSA-N
assay   ≥99.0% (T)
drug control   regulated under CDSA - not available from Sigma-Aldrich Canada
ign. residue   ≤0.1%
mp   121-123 °C(lit.)
  121-123 °C
solubility   hot water: soluble0.5 g/10 mL, clear, colorless to faintly yellow

Description

Packaging

50, 250 g in poly bottle

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.

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.

Price and Availability

Suggested Laboratory Gloves


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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Knoevenagel Condensation Reaction

The Knoevenagel Condensation Reaction is a classic organic synthesis, described by Emil Knoevenagel in the 1890’s. The Knoevenagel reaction is a modified Aldol Condensation with a nucleophilic additi...
Keywords: Aldol condensation, C-C bond formation, Condensations, Dehydration reaction, Knoevenagel Condensation, Nucleophilic additions, Organic synthesis

Peer-Reviewed Papers
15

References

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