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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:
769-42-6
Molecular Weight:
156.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57649861
EC Number:
212-211-7
Beilstein/REAXYS Number:
139810
MDL number:
MFCD00006675
Assay:
≥99.0% (T)
Form:
solid
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Quality Level

200

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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pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6755V
WXBF6232V
WXBF5304V
WXBF4949V
WXBF3419V

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Articles

Knoevenagel Condensation Reaction

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.

María Victoria Roux et al.
The journal of physical chemistry. A, 115(14), 3167-3173 (2011-03-25)
This paper reports an experimental and computational thermochemical study on 1,3-dimethylbarbituric acid. The value of the standard (p° = 0.1 MPa) molar enthalpy of formation in the gas phase at T = 298.15 K has been determined. The energy of
Burkhard Knopf et al.
Environmental science and pollution research international, 28(13), 16244-16252 (2020-12-18)
Cyanide compounds are naturally emitted into the environment in low levels by degradation processes or emitted from anthropogenic sources. In surface water, complex cyanide compounds as well as "free cyanide" are present. The latter term covers hydrogen cyanide and cyanide
Malek Taher Maghsoodlou et al.
Molecular diversity, 15(1), 227-231 (2010-07-14)
5-Aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives were obtained by in situ reaction alkyl or aryl isocyanides and pyridinecarbaldehyde derivatives in the presence of 1,3-dimethylbarbituric acid in dichloromethane without any prior activation or modifications.
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Global Trade Item Number

SKUGTIN
39565-50G04061831983098
39565-250G04061831983081