39565
1,3-Dimethylbarbituric acid
≥99.0% (T)
Synonym(s):
1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
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About This Item
Empirical Formula (Hill Notation):
C6H8N2O3
CAS Number:
Molecular Weight:
156.14
Beilstein:
139810
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Bor-Cherng Hong et al.
Organic letters, 14(2), 448-451 (2011-12-27)
Synthesis of isochromene pyrimidinedione derivatives having five stereocenters has been achieved by a one-pot Michael-Knoevenagel condensation-inverse-electron-demand hetero-Diels-Alder reaction of α, β-unsaturated aldehydes, olefinic nitroalkanes, and 1,3-dimethylbarbituric acid via a one-pot strategy with excellent diastereo- and enantioselectivities (up to 99% ee).
Dipak Samanta et al.
Chemical communications (Cambridge, England), 49(39), 4307-4309 (2013-01-09)
Unique three-component self-assembly of a cis-blocked 90° Pd(II) acceptor with a mixture of tri- and tetra-imidazole donors led to the self-sorting of a Pd7 molecular boat with an internal nanocavity, which catalyses the Knoevenagel condensation of a series of aromatic
Christian Löfberg et al.
Chemical communications (Cambridge, England), (48)(48), 5000-5002 (2006-12-06)
Microwave assisted indirect functionalization of alcohols with 1,3-dimethylbarbituric acid followed by spirocyclisation employing a sequential one-pot Ir(III)/Pd(0) catalysed process, involving the formation of three new C-C bonds, one spirocyclic ring and one di- or tri-substituted exocyclic alkene, is described.
1, 3-Dimethylbarbituric Acid
Argintaru OA.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2011)
Shahram Lotfi et al.
Materials science & engineering. C, Materials for biological applications, 76, 153-160 (2017-05-10)
Electrochemical oxidation of trimipramine in the absence and presence of 1,3 dimethyl barbituric acid as a nucleophile in aqueous solution has been studied using cyclic voltammetry and controlled-potential coulometry electrolysis. Voltammetric studies of electro-oxidation of trimipramine were realized in a
Articles
Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.
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