Meldrum's acid

Meldrum's acid
Meldrum's Acid
Names
Preferred IUPAC name
2,2-Dimethyl-1,3-dioxane-4,6-dione
Other names
Isopropylidene malonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.358 Edit this at Wikidata
UNII
  • InChI=1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3 ☒N
    Key: GXHFUVWIGNLZSC-UHFFFAOYSA-N ☒N
  • InChI=1/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
    Key: GXHFUVWIGNLZSC-UHFFFAOYAM
  • InChI=1/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
    Key: GXHFUVWIGNLZSC-UHFFFAOYAM
  • O=C1OC(OC(=O)C1)(C)C
Properties
C6H8O4
Molar mass 144.126 g·mol−1
Melting point 94 to 95 °C (201 to 203 °F; 367 to 368 K) (decomposes)[1]
Acidity (pKa) 4.97
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Meldrum's acid or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound with formula C6H8O4. Its molecule has a heterocyclic core with four carbon and two oxygen atoms; the formula can also be written as [−O−(C(CH3)2)−O−(C=O)−(CH2)−(C=O)−].

It is a crystalline colorless solid, sparingly soluble in water. It decomposes on heating with release of carbon dioxide and acetone.[2][3]

  1. ^ "Meldrum's Acid". The Merck Index. 14th. Vol. edition. Merck Research Laboratories. 2006. p. 1005. ISBN 978-0-911910-00-1.
  2. ^ McNab, Hamish (1978). "Meldrum's acid". Chemical Society Reviews. 7 (3): 345–358. doi:10.1039/CS9780700345.
  3. ^ Cite error: The named reference meldrum was invoked but never defined (see the help page).