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39565

Sigma-Aldrich

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
Beilstein:
139810
EC Number:
212-211-7
MDL number:
MFCD00006675
UNSPSC Code:
12352100
PubChem Substance ID:
57649861
NACRES:
NA.22

Quality Level

200

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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

39565-VAR:
39565-50G:
39565-6X250G:
39565-BULK:
39565-250G:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6344V
WXBD6201V
WXBD5549V
WXBD4044V
WXBD3044V

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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
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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.

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