210145
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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Fórmula empírica (notación de Hill):
C6H8O4
Número CAS:
Peso molecular:
144.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
217-992-8
Beilstein/REAXYS Number:
117310
MDL number:
Assay:
98%
Form:
solid
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Permítanos ayudarleInChI key
GXHFUVWIGNLZSC-UHFFFAOYSA-N
InChI
1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
SMILES string
CC1(C)OC(=O)CC(=O)O1
assay
98%
form
solid
Quality Level
solubility
dioxane: soluble 5%, clear to very slightly hazy, colorless to faintly yellow
functional group
ester, ketal
storage temp.
2-8°C
Categorías relacionadas
General description
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. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.
Meldrum′s acid is used as a valuable starting material to synthesize heterocycles and as intermediates in organic synthesis reactions.
Meldrum′s acid is used as a valuable starting material to synthesize heterocycles and as intermediates in organic synthesis reactions.
Application
2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:
- macrocyclic β-keto lactone
- 4-pyridyl-substituted heterocycles
- 2-substituted indoles
- isofraxidin.
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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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