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Diethyl phenylmalonate

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Diethyl phenylmalonate
Diethyl phenylmalonate
Names
IUPAC name Diethyl phenylmalonate
Other names Diethyl phenylpropanedioate; Propanedioic acid 2-phenyl- diethyl ester; Diethyl-phenylmalonat
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 614465
ChemSpider
ECHA InfoCard 100.001.324 Edit this at Wikidata
EC Number
  • 201-456-5
PubChem CID
UNII
CompTox Dashboard (EPA)
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,3-4H2,1-2H3Key: FGYDHYCFHBSNPE-UHFFFAOYSA-N
SMILES
  • CCOC(=O)C(C1=CC=CC=C1)C(=O)OCC
Properties
Chemical formula C13H16O4
Molar mass 236.267 g·mol
Density 1.096 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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

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. This indirect method is often used because aryl halides are relatively weaker electrophiles than alkyl halides and thus poorly alkylate diethyl malonate. Methods using Caesium carbonate and copper(I) iodide have been developed to overcome this difficulty however.

References

  1. Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry: 11. doi:10.1002/14356007.a13_533. ISBN 3527306730.
  2. Meyer, G. M.; Levene, P. A. (1936). "Diethyl phenylmalonate". Organic Syntheses. 16: 33. doi:10.15227/orgsyn.016.0033.
  3. Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp. 1174–1179. ISBN 9780582462366.
  4. Hennessy, Edward J.; Buchwald, Stephen L. (2002). "A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate". Organic Letters. 4 (2): 269–272. doi:10.1021/ol017038g. PMID 11796067.
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