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Names | |
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IUPAC name Diethyl phenylmalonate | |
Other names Diethyl phenylpropanedioate; Propanedioic acid 2-phenyl- diethyl ester; Diethyl-phenylmalonat | |
Identifiers | |
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3D model (JSmol) | |
614465 | |
ChemSpider |
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ECHA InfoCard | 100.001.324 ![]() |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C13H16O4 | |
Molar mass | 236.267 g·mol−1 |
Density | 1.096 g/cm3 |
Melting point | 16.5 °C (61.7 °F; 289.6 K) |
Boiling point | 170–172 °C (338–342 °F; 443–445 K) (14 mmHg) |
Refractive index (nD) | n20/D 1.491 |
Hazards | |
Flash point | 120 |
Safety data sheet (SDS) | MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diethyl phenylmalonate is an aromatic malonic ester used in the synthesis of moderate to long lasting barbiturates such as phenobarbital.[1]
Unlike other malonic esters that are derived via malonic ester synthesis, diethyl phenylmalonate is typically indirectly derived via a Claisen condensation with diethyl oxalate and ethyl phenylacetate followed by decarbonylation.[2] This indirect method is often used because aryl halides are relatively weaker electrophiles than alkyl halides and thus poorly alkylate diethyl malonate.[3] Methods using Caesium carbonate and copper(I) iodide have been developed to overcome this difficulty however.[4]