210145

2,2-Dimethyl-1,3-dioxane-4,6-dione

98%

• Synonym(s): Malonic acid cyclic isopropylidene ester, Meldrum’s acid, cycl-Isopropylidene malonate
• 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

Properties

• 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

Description

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 (pK_a 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.

Safety Information

• 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