Diethyl phenylmalonate
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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) |
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Beilstein Reference | 614465 |
ChemSpider |
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ECHA InfoCard | 100.001.324 ![]() |
EC Number |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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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 compound
Diethyl phenylmalonate is an aromatic malonic ester used in the synthesis of moderate to long lasting barbiturates such as phenobarbital.[1]
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]
References
- ^ Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry: 11. doi:10.1002/14356007.a13_533. ISBN 3527306730.
- ^ Meyer, G. M.; Levene, P. A. (1936). "Diethyl phenylmalonate". Organic Syntheses. 16: 33. doi:10.15227/orgsyn.016.0033.
- ^ 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.
- ^ 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.