2,2,5-Trimethyl-1,3-dioxane-4,6-dione, CAS No. 3709-18-0

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3709-18-0

Catalog No. EBD53431

CAS 3709-18-0

Name 2,2,5-Trimethyl-1,3-dioxane-4,6-dione

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Basic Information

Synonyms: Methylmalonicacidcyclicisopropylideneester cycl-Isopropylidenemethylmalonate Methylmeldrum'sacid 2,2,5-Trimethyl-1,3-dioxane-4,6-dione MethylMeldrumsacid

Molecular Formula: C7H10O4

Molecular Weight: 158.15

MDL Number: MFCD00006637

Categories: Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters Synthetic Chemistry > Basic Synthetic Reagents > C-C Bond Formation Reagents

Product Description:

Isopropylidene methylmalonate is a diester derivative of methylmalonic acid, specifically the isopropylidene acetal of methylmalonic acid. It is a versatile reagent in organic synthesis, characterized by its activated methylene group flanked by two ester functionalities and protected as a cyclic acetal. Its primary application is as a building block for the synthesis of various complex molecules. The activated methylene group can undergo alkylation reactions, allowing for the introduction of substituents. Subsequent deprotection and decarboxylation steps enable the conversion of this reagent into substituted acetic acid derivatives, α-keto esters, or other valuable intermediates. It is particularly useful in the synthesis of pharmaceuticals, agrochemicals, and natural products where the construction of quaternary carbon centers or specific carboxylic acid frameworks is required. This compound serves as a fundamental carbon-carbon bond forming reagent and a protected synthon, making it a valuable tool in methodological development and target-oriented synthesis within research and industrial chemistry laboratories.

Physical Properties

Melting Point: 111-114 °C(lit.)

Boiling Point: 343.6 °C at 760 mmHg

Flash Point: 183.4 °C

Density: 1.13 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: White to slightly pink crystalline powder