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39565

Sigma-Aldrich

1,3-Dimethylbarbituric acid

≥99.0% (T)

Synonim(y):

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

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About This Item

Wzór empiryczny (zapis Hilla):
C6H8N2O3
Numer CAS:
769-42-6
Masa cząsteczkowa:
156.14
Beilstein:
139810
Numer WE:
212-211-7
Numer MDL:
MFCD00006675
Kod UNSPSC:
12352100
Identyfikator substancji w PubChem:
57649861
NACRES:
NA.22
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Poziom jakości

200

Próba

≥99.0% (T)

Formularz

solid

pozostałość po prażeniu

≤0.1%

mp

121-123 °C (lit.)
123-126 °C

rozpuszczalność

hot water: soluble 0.5 g/10 mL, clear, colorless to faintly yellow

ciąg SMILES

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

Klucz InChI

VVSASNKOFCZVES-UHFFFAOYSA-N

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Opis ogólny

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.[1] It undergoes self-sorted Pd7 molecular boat having an internal nanocavity (catalyst)-assisted Knoevenagel condensation reaction with various aromatic aldehydes.[1] 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.[2]

Zastosowanie

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.[3]
  • Synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives.[4]
  • Microwave promoted indirect functionalization of alcohols, via spirocyclisation employing a sequential one-pot Ir(III)/Pd(0) catalyzed process.[5]
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Piktogramy

CorrosionExclamation mark
GHS05,GHS07

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H302,H318

Zwroty wskazujące środki ostrożności

P264 - P270 - P280 - P301 + P312 - P305 + P351 + P338 - P501

Klasyfikacja zagrożeń

Acute Tox. 4 Oral - Eye Dam. 1

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 1

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

dust mask type N95 (US), Eyeshields, Gloves

Wybierz jedną z najnowszych wersji:

Certyfikaty analizy (CoA)

Lot/Batch Number
WXBF5304V
WXBF4949V
WXBF3419V
WXBF4111V
WXBF3992V

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4-Aminoantipyrine analytical standard

Supelco

43827

4-Aminoantipyrine

4-Aminoantipyrine reagent grade

Sigma-Aldrich

A4382

4-Aminoantipyrine

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
1, 3-Dimethylbarbituric Acid
Argintaru OA.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2011)
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.
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
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).
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Produkty

Reakcja kondensacji Knoevenagela

Kondensacja Knoevenagela to reakcja organiczna nazwana na cześć Emila Knoevenagela. Jest to klasyczna reakcja tworzenia wiązań C-C i modyfikacja kondensacji aldolowej.

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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