Diethyl phenylmalonate

Diethyl phenylmalonate is an aromatic malonic ester used in the synthesis of moderate to long lasting barbiturates such as phenobarbital.^[1]

Diethyl phenylmalonate

Diethyl phenylmalonate
Names
IUPAC name Diethyl phenylmalonate
Other names Diethyl phenylpropanedioate; Propanedioic acid 2-phenyl- diethyl ester; Diethyl-phenylmalonat
Identifiers
CAS Number	83-13-6 Y
3D model (JSmol)	Interactive image
Beilstein Reference	614465
ChemSpider	59885 Y
ECHA InfoCard	100.001.324
EC Number	201-456-5
PubChem CID	66514
UNII	XVQ6PE5CLT Y
CompTox Dashboard (EPA)	DTXSID7058886
InChI InChI=1S/C13H16O4/c1-3-16-12(14)11(13(15)17-4-2)10-8-6-5-7-9-10/h5-9,11H,3-4H2,1-2H3 Y Key: FGYDHYCFHBSNPE-UHFFFAOYSA-N Y
SMILES CCOC(=O)C(C1=CC=CC=C1)C(=O)OCC
Properties
Chemical formula	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). Infobox references

Chemical synthesis

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]