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| 2,2-Dimethyl-1,3-dioxane-4,6-dione Basic information |
| 2,2-Dimethyl-1,3-dioxane-4,6-dione Chemical Properties |
| Melting point | 92-96 °C(lit.) | | Boiling point | 182.71°C (rough estimate) | | density | 1.1311 (rough estimate) | | vapor pressure | 0.044-133Pa at 25℃ | | refractive index | 1.4434 (estimate) | | storage temp. | 2-8°C | | solubility | dioxane: soluble5%, clear to very slightly hazy, colorless to faintly yellow | | pka | 5.1(at 25℃) | | form | Crystals or Powder | | color | Brownish-white to beige-brown | | Water Solubility | 2.5 g/100 mL (20 ºC) | | Merck | 14,5817 | | BRN | 117310 | | InChIKey | GXHFUVWIGNLZSC-UHFFFAOYSA-N | | LogP | -1.58-4.786 at 25℃ | | CAS DataBase Reference | 2033-24-1(CAS DataBase Reference) | | NIST Chemistry Reference | 1,3-Dioxane-4,6-dione, 2,2-dimethyl-(2033-24-1) | | EPA Substance Registry System | 1,3-Dioxane-4,6-dione, 2,2-dimethyl- (2033-24-1) |
| 2,2-Dimethyl-1,3-dioxane-4,6-dione Usage And Synthesis |
| Chemical Properties | Crystals, white to beige | | Uses | Meldrum`s acid is an intermediate for different organic syntheses. For typical reactions please consult the Meldrum`s acid brochure, which you can order. Contact us. Product Data Sheet | | Uses | An antimicrobial agent | | Uses | In organic synthesis as a substitute for acyclic malonic esters and generally as a C3O2 synthon. | | Uses | 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.
| | Preparation | 2,2-Dimethyl-1,3-dioxane-4,6-dione is usually prepared by condensation of malonic acid with acetone in acetic anhydride in the presence of sulfuric acid. Excellent yield of the product was achieved when acetic anhydride was added in a slow, controlled manner to a mixture of acetone, malonic acid and an acid catalyst. | | Synthesis Reference(s) | Journal of the American Chemical Society, 70, p. 3426, 1948 DOI: 10.1021/ja01190a060 | | 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. | | Flammability and Explosibility | Nonflammable | | Purification Methods | Crystallise the dione from Me2CO/H2O. It is a synthon for the C3 malonic acid moiety. [Arnette et al. J Am Chem Soc 106 6759 1984, Bihlmayer et al. Monatsh Chem 98 564 1967, Review: McNab Chem Soc, Rev 7 345 1978, Chan & Huang Synthesis 452 1982, Beilstein 19/5 V 8.] |
| 2,2-Dimethyl-1,3-dioxane-4,6-dione Preparation Products And Raw materials |
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