Ethyl diacetoacetate, CAS No. 603-69-0

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603-69-0

Catalog No. EBD3670

CAS 603-69-0

Name Ethyl diacetoacetate

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Basic Information

Synonyms: Ethyl2-acetylacetoacetate 3-Ethoxycarbonylacetylacetone Ethyldiacetoacetate Ethyldiacetoacetate,(3-Ethoxycarbonylacetylacetone) Diethyldiacetoacetate 2-Acetylacetoaceticacidethylester ethyl2-acetyl-3-oxobutanoate 3-[ethoxy(hydroxy)methylidene]pentane-2,4-dione

Molecular Formula: C8H12O4

Molecular Weight: 172.18

MDL Number: MFCD00009864

Categories: Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks Synthetic Chemistry > Basic Synthetic Reagents > C-C Bond Formation Reagents

Product Description:

Ethyl diacetoacetate is an organic compound with the molecular formula C10H16O6. It is a diester derivative of acetoacetic acid, featuring two acetoacetate groups linked by a central carbon atom. This structure makes it a versatile building block in organic synthesis, particularly valued for its ability to undergo multiple condensation and cyclization reactions. Its primary application is as a key intermediate in the synthesis of various heterocyclic compounds, especially pyridines and pyrimidines. It serves as a crucial precursor for pharmaceuticals, agrochemicals, and dyes. The compound is frequently used in Hantzsch-type syntheses to produce dihydropyridines, which are important scaffolds for calcium channel blockers and other bioactive molecules. Its reactivity stems from the active methylene groups flanked by carbonyls, allowing it to act as a carbon nucleophile in C-C bond formation. As a specialized synthetic reagent, it is less common than simple acetoacetate esters but is commercially available for targeted research and development purposes. Handling requires standard precautions for organic esters, including adequate ventilation and avoidance of strong oxidizers.

Physical Properties

Boiling Point: 104-105 °C/17 mmHg(lit.)

Flash Point: 85 °C

Density: 1.104 g/mL at 25 °C(lit.)

Refractivity: n20/D 1.47(lit.)

Analytical Data

Appearance: clear colorless to yellow liquid