Diethyl 2-(2-phenylacetyl)malonate
[CAS# 20320-59-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aromatic carboxylic acid ester
• Name: Diethyl 2-(2-phenylacetyl)malonate
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30
• CAS Registry Number: 20320-59-6
• SMILES: CCOC(=O)C(C(=O)CC1=CC=CC=C1)C(=O)OCC

Properties

• Solubility: 923.2 mg/L (25 ºC water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.504, Calc.^*
• Melting point: 15.73 ºC
• Boiling Point: 356.3±27.0 ºC (760 mmHg), Calc.^*, 342.09 ºC
• Flash Point: 154.0±23.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

Diethyl 2-(2-phenylacetyl)malonate, a compound also known as phenylacetone malonate, was discovered through organic chemistry research aimed at synthesizing new molecules with potential pharmaceutical applications. The synthesis involves the reaction of phenylacetic acid with diethyl malonate, resulting in the formation of the desired compound.

Diethyl 2-(2-phenylacetyl)malonate serves as a valuable intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a versatile building block for the production of various drugs, including analgesics, antihypertensives, and anticonvulsants. Chemical modifications of the phenylacetyl or malonate groups enable the creation of drug candidates with improved efficacy, bioavailability, or selectivity.

In synthetic organic chemistry, diethyl 2-(2-phenylacetyl)malonate is widely used as a precursor for the synthesis of complex organic molecules. Its functional groups and reactivity make it suitable for various transformations, including condensation reactions, alkylation, and cyclization processes. Chemists utilize this compound to introduce the phenylacetyl group into target molecules.

Diethyl 2-(2-phenylacetyl)malonate plays a crucial role in medicinal chemistry research, where it is employed for structure-activity relationship studies and lead optimization efforts. By synthesizing analogs and derivatives of known bioactive compounds using this building block, researchers can explore the effects of structural modifications on biological activity, pharmacokinetics, and drug-likeness properties.

Beyond its established applications, ongoing research explores new uses for diethyl 2-(2-phenylacetyl)malonate in drug discovery, materials science, and chemical biology. Scientists investigate its reactivity, properties, and potential interactions with biological targets to develop innovative therapies for treating diseases and disorders.

Diethyl 2-(2-phenylacetyl)malonate serves as a valuable educational tool in organic chemistry laboratories and academic research settings. Its synthesis and manipulation provide students and researchers with practical experience in synthetic organic chemistry techniques, including functional group transformations, purification methods, and spectroscopic analysis.