210145
2,2-Dimethyl-1,3-dioxane-4,6-dione
98%
Synonym(s):
Malonic acid cyclic isopropylidene ester, Meldrum’s acid, cycl-Isopropylidene malonate
Sign In to View Organizational & Contract Pricing.
Select a Size
About This Item
Empirical Formula (Hill Notation):
C6H8O4
CAS Number:
Molecular Weight:
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
InChI 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
Related Categories
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.
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Martin Wolffs et al.
Chemical communications (Cambridge, England), 47(38), 10572-10574 (2011-09-01)
A facile, ketene-based strategy for the synthesis of polyesters from stable Meldrum's acid monomers has been developed which overcomes many issues associated with traditional step-growth procedures. A significant increase in polymerization efficiency is observed with only 10 min reaction time
Synthetic Communications, 23, 1147-1147 (1993)
Henning H-G, et al.
Justus Liebigs Annalen der Chemie, 813-813 (1992)
New route to 2-substituted indoles by pyrolysis of N-acylacetylphenylhydroxylamines.
Hirao K-I, et al.
Tetrahedron Letters, 33(11), 1459-1462 (1992)
Tetrahedron, 63, 389-389 (2007)
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