Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

210145

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

functional group

ester

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

Looking for similar products? Visit Product Comparison Guide

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.

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
STBJ3104
STBF4868V
STBG8233
STBD6952V
STBD1211V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

1,3-Dimethylbarbituric acid ≥99.0% (T)

Sigma-Aldrich

39565

1,3-Dimethylbarbituric acid

Aaron M Dumas et al.
Accounts of chemical research, 43(3), 440-454 (2009-12-17)
Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) is a molecule with a unique history, owing to its originally misassigned structure, as well as a unique place among acylating agents, owing to its high acidity and remarkable electrophilicity. In this Account, we outline the work
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)
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)
View All Related Papers

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.

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