Diethylmalonate (DEM) is an organic compound with the chemical formula C₈H₁₀O₄. It is a colorless to pale yellow liquid with a fruity odor. Diethylmalonate is a malonate ester and is widely used in organic synthesis as a building block in the production of various chemicals, pharmaceuticals, and agrochemicals. It is a versatile intermediate in the synthesis of a wide range of compounds, including α,β-unsaturated carbonyl compounds, heterocyclic compounds, and other biologically active molecules.
Properties of Diethylmalonate:
- Molecular Formula: C₈H₁₀O₄
- Molar Mass: 174.17 g/mol
- CAS Number: 105-53-3
- Functional Groups: Ester group (-COO-) and malonate group (-CH₂CO₂Et).
- Reactivity:
- Diethylmalonate contains two ester functional groups, making it highly reactive in nucleophilic substitution and alkylation reactions.
- It is commonly used in Michael additions, aldol condensations, and other synthetic organic transformations.
- The methine hydrogen (–CH₂) in the malonate group is highly acidic, which makes Diethylmalonate a good nucleophile for alkylation and addition reactions.
- Diethylmalonate undergoes hydrolysis to form malonic acid when exposed to acidic or basic conditions.
- Appearance: A colorless to pale yellow liquid with a fruity odor.
- Density: 1.039 g/cm³ at 20°C.
- Melting Point: −49°C (−56°F).
- Boiling Point: 199°C (390°F).
- Solubility:
- Soluble in organic solvents such as ether, alcohol, and acetone.
- Slightly soluble in water, but it is more soluble in polar organic solvents.
Uses of Diethylmalonate:
- Pharmaceuticals: Used in the synthesis of barbiturates and other drugs.
- Flavors and Fragrances: Used as an intermediate in flavor and fragrance production.
- Chemical Synthesis: Used in organic synthesis and as a reagent in reactions like Michael addition.