ChemicalBook Product Catalog Chemical Reagents Organic reagents aliphatic ketones 2,2-Dimethyl-1,3-dioxane-4,6-dione

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

2,2-Dimethyl-1,3-dioxane-4,6-dione Basic information
Product Name:2,2-Dimethyl-1,3-dioxane-4,6-dione
Synonyms:'MELDRUM'S ACID';LABOTEST-BB LT00233174;2,2-DiMethyl-1,3-dioxane-4,6-dione, 98% 25GR;2,2-Dimethyl-1,3-dioxane-4,6-dione cycl-Isopropylidene Malonate Malonic Acid Cyclic Isopropylidene Ester;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
CAS:2033-24-1
MF:C6H8O4
MW:144.13
EINECS:217-992-8
Product Categories:Drug Discovery;Dioxanes;Dioxanes & Dioxolanes;pharmaceutical intermediates;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;2033-24-1
Mol File:2033-24-1.mol
2,2-Dimethyl-1,3-dioxane-4,6-dione Structure
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
pka5.1(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
InChIKeyGXHFUVWIGNLZSC-UHFFFAOYSA-N
LogP-1.58-4.786 at 25℃
CAS DataBase Reference2033-24-1(CAS DataBase Reference)
NIST Chemistry Reference1,3-Dioxane-4,6-dione, 2,2-dimethyl-(2033-24-1)
EPA Substance Registry System1,3-Dioxane-4,6-dione, 2,2-dimethyl- (2033-24-1)
Safety Information
Hazard Codes Xi,T
Risk Statements 36/37/38-45
Safety Statements 37/39-24/25-53-45-36-26
WGK Germany 3
RTECS JH0800000
F 10-21
TSCA Yes
HazardClass IRRITANT
HS Code 29322090
MSDS Information
ProviderLanguage
2,2-Dimethyl-1,3-dioxane-4,6-dione English
SigmaAldrich English
ACROS English
ALFA English
2,2-Dimethyl-1,3-dioxane-4,6-dione Usage And Synthesis
DescriptionMeldrum's acid, also known as 2,2-dimethyl-1,3-dioxane-4,6-dione, is an organic compound with the formula C6H8O4. 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 PropertiesThe compound appears as white to beige crystals. It has a melting point of 94-95℃ (decomposition), is insoluble in water, and is soluble in ethanol and acetone.
Application2,2-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.
UsesMeldrum's acid serves as an intermediate in a variety of organic synthesis reactions. It is commonly used as an alternative to acyclic malonic esters and generally acts as a C3O2 synthon in organic synthesis.
UsesAn antimicrobial agent
Preparation2,2-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 Description2,2-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 ExplosibilityNonflammable
Purification MethodsCrystallise 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 [5-14C] Diisopropyl malonate 5-DIAZOMELDRUM'S ACID 2,5-Dimethylpyrrolidine Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid 1,2-Dioxane 5-({[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]amino}methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 5-(4,5-dimethyl-1,3-dithiol-2-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione BIS(METHYLTHIO)METHYLENE MELDRUMS ACID DIMETHYLGLYOXIME DISODIUM SALT 5-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione,5-[(4-Hydroxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 5-(2-Chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione,5-[(2-Chlorophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 5-[1-(Methylthio)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 5-({5-nitro-2-furyl}methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 5-(4-Methoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione,5-(p-Methoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione BUTYL OLEATE
Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.