| Identification | More | [Name]
2,2-Dimethyl-1,3-dioxane-4,6-dione | [CAS]
2033-24-1 | [Synonyms]
2,2-DIMETHYL-1,3-DIOXAN-4,6-DIONE
2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
AKOS B029723
CYCLIC-ISOPROPYLIDENE MALONATE
CYCL-ISOPROPYLIDENE MALONATE
ISOPROPYLIDENE MALONATE
LABOTEST-BB LT00233174
MALONIC ACID CYCLIC ISOPROPYLIDENE ESTER
MELDRUMS ACID
'MELDRUM'S ACID'
MELDRUM'S ACID
SUB-ISOPROPYL MALONATE
2,2-dimethyl-1,3-dioxane-4,6-diacetone
2,2-Dimethyl-4,6-dioxo-m-dioxane
2,2-Dimethyl-m-dioxane-4,6-dione
2,2-dimethyl-m-dioxane-6-dione
4,6-Diketo-2,2-dimethyl-1,3-dioxane
6-dione,2,2-dimethyl-3-dioxane-4
m-Dioxane-4,6-dione, 2,2-dimethyl-
Meldrumacid | [EINECS(EC#)]
217-992-8 | [Molecular Formula]
C6H8O4 | [MDL Number]
MFCD00006638 | [Molecular Weight]
144.13 | [MOL File]
2033-24-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystals, white to beige | [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. ]
0-6°C | [solubility ]
dioxane: soluble5%, clear to very slightly hazy, colorless to faintly yellow | [form ]
Crystals or Powder | [pka]
5.1(at 25℃) | [color ]
Brownish-white to beige-brown | [Water Solubility ]
2.5 g/100 mL (20 ºC) | [Usage]
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 | [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) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
2033-24-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R45:May cause cancer. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S24/25:Avoid contact with skin and eyes .
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
JH0800000
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29322000 |
| Hazard Information | Back Directory | [Description]
Meldrum's acid(2033-24-1) or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound. The compound was first made in 1908 by Andrew Norman Meldrum by a condensation reaction of malonic acid with acetone in acetic anhydride and sulfuric acid. Meldrum misidentified the structure as a β-lactone of β-hydroxyisopropylmalonic acid. Yet Meldrum's acid has a high acidity with a pKa of 4.97, because like ascorbic acid, deprotonation at the methylene next to the carbonyls produces a stable enolate. Because of this property Meldrum's acid like malonic acid is a reactant in Knoevenagel condensations.
| [Chemical Properties]
Crystals, white to beige | [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. | [Uses]
An antimicrobial agent | [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 | [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 (2033-24-1) 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.] |
| Spectrum Detail | Back Directory | [Spectrum Detail]
2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)MS
2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)1HNMR
2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)13CNMR
2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)IR1
2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)IR2
2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)Raman
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