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Sigma-Aldrich

2,2-Dimethyl-1,3-dioxane-4,6-dione

2,2-Dimethyl-1,3-dioxane-4,6-dione

98%

Sinónimos:

Malonic acid cyclic isopropylidene ester, Meldrum’s acid, cycl-Isopropylidene malonate

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10 G
US$ 37,50
25 G
US$ 67,60
100 G
US$ 159,00

US$ 37,50

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10 G
US$ 37,50
25 G
US$ 67,60
100 G
US$ 159,00

About This Item

Fórmula empírica (notación de Hill):
C6H8O4
Número de CAS:
2033-24-1
Peso molecular:
144.13
Beilstein:
117310
Número CE:
217-992-8
Número MDL:
MFCD00006638
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24852618
NACRES:
NA.22

US$ 37,50

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Nivel de calidad

200

Ensayo

98%

Formulario

solid

mp

92-96 °C (lit.)

solubilidad

dioxane: soluble 5%, clear to very slightly hazy, colorless to faintly yellow

grupo funcional

ester
ketal

temp. de almacenamiento

2-8°C

cadena SMILES

CC1(C)OC(=O)CC(=O)O1

InChI

1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3

Clave InChI

GXHFUVWIGNLZSC-UHFFFAOYSA-N

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Descripción general

2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pKa 4.83) and steric rigidity[1]. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.[2]

Meldrum′s acid is used as a valuable starting material to synthesize heterocycles and as intermediates in organic synthesis reactions.[3][4]

Aplicación

2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:
  • macrocyclic β-keto lactone[5]
  • 4-pyridyl-substituted heterocycles[6]
  • 2-substituted indoles[7]
  • isofraxidin.[8]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
BCCH9274
STBJ3104
STBF4868V
STBG8233
STBD6952V

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New multicomponent domino reactions (MDRs) in water: highly chemo-, regio-and stereoselective synthesis of spiro {[1, 3] dioxanopyridine}-4, 6-diones and pyrazolo [3, 4-b] pyridines.
Ma N, et al.
Green Chemistry, 12?(8), 1357-1361 (2010)
Songlei Zhu et al.
Molecules (Basel, Switzerland), 17(12), 13856-13863 (2012-11-24)
A series of 4-aryl-6-methyl-3,4-dihydro-2H-pyrano[3,2-c]quinolin-2,5(6H)-diones were synthesized via the three-component reactions of aromatic aldehydes, 4-hydroxy-1-methylquinolin-2(1H)-one, and Meldrum's acid catalyzed by L-proline. The structures of the products were identified by spectroscopic analysis. A mechanism for this three-component reaction catalyzed by L-proline was
Davood Nematollahi et al.
Chemical & pharmaceutical bulletin, 58(1), 23-26 (2010-01-05)
Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates
The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives.
Lermer L, et al.
Canadian Journal of Chemistry, 70(5), 1427-1445 (1992)
Characterization of Meldrum?s acid derivative 5-(5-Ethyl-1, 3, 4-thiadiazol-2-ylamino) methylene-2, 2-dimethyl-1, 3-dioxane-4, 6-dione by Raman and FT-IR spectroscopy and DFT calculations
De Toledo TA, et al.
Journal of Molecular Structure, 37-42, 1091-1091 (2015)
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Artículos

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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