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Sigma-Aldrich

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:
2033-24-1
Molecular Weight:
144.13
Beilstein:
117310
EC Number:
217-992-8
MDL number:
MFCD00006638
UNSPSC Code:
12352100
PubChem Substance ID:
24852618
NACRES:
NA.22

Assay

98%

form

solid

mp

92-96 °C (lit.)

solubility

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

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Liam Payne et al.
Molecules (Basel, Switzerland), 25(21) (2020-10-30)
Donor-acceptor Stenhouse adducts (DASAs) are a novel class of solvatochromic photoswitches with increasing importance in photochemistry. Known for their reversibility between open triene and closed cyclized states, these push-pull molecules are applicable in a suite of light-controlled applications. Recent works
Sheng Cui et al.
Journal of the American Chemical Society, 132(2), 436-437 (2009-12-22)
The enantioselective conjugate addition of alkynyl nucleophiles has been a long-standing challenge in synthetic chemistry. This paper describes a highly practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors using cinchonidine (<$100/kg) as the chiral mediator. The process provides practical access
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)
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
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Articles

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.

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.

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.

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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