Chemistry:Diethyl phenylmalonate
From HandWiki
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| Names | |
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| IUPAC name
Diethyl phenylmalonate
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| Other names
Diethyl phenylpropanedioate; Propanedioic acid 2-phenyl- diethyl ester; Diethyl-phenylmalonat
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| Identifiers | |
3D model (JSmol)
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| 614465 | |
| ChemSpider | |
| EC Number |
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PubChem CID
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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)
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n20/D 1.491 |
| Hazards | |
| Safety data sheet | MSDS |
| Flash point | 120 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
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. https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd.
- ↑ 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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