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About This Item
Empirical Formula (Hill Notation):
C6H8N2O3
CAS Number:
Molecular Weight:
156.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-211-7
Beilstein/REAXYS Number:
139810
MDL number:
Assay:
≥99.0% (T)
Form:
solid
Quality Segment
assay
≥99.0% (T)
form
solid
ign. residue
≤0.1%
mp
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
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.
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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