210145
2,2-Dimethyl-1,3-dioxane-4,6-dione
98%
Synonym(s):
Malonic acid cyclic isopropylidene ester, Meldrum’s acid, cycl-Isopropylidene malonate
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About This Item
Empirical Formula (Hill Notation):
C6H8O4
CAS Number:
Molecular Weight:
144.13
Beilstein:
117310
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
form
solid
mp
92-96 °C (lit.)
solubility
dioxane: soluble 5%, clear to very slightly hazy, colorless to faintly yellow
functional group
ester
ketal
storage temp.
2-8°C
SMILES string
CC1(C)OC(=O)CC(=O)O1
InChI
1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
InChI key
GXHFUVWIGNLZSC-UHFFFAOYSA-N
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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 Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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