Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

39565

Sigma-Aldrich

1,3-Dimethylbarbituric acid

≥99.0% (T)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

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

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF3419V
WXBF4111V
WXBF3992V
WXBF4405V
WXBF2336V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Barbituric acid for synthesis

Sigma-Aldrich

8.00133

Barbituric acid

4-Aminoantipyrine analytical standard

Supelco

43827

4-Aminoantipyrine

4-Aminoantipyrine reagent grade

Sigma-Aldrich

A4382

4-Aminoantipyrine

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
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
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
View All Related Papers

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.

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.

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.

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service