Ethyl diazoacetate
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| Names | |
|---|---|
| IUPAC name
Ethyl diazoacetate | |
| Other names
2-diazoacetic acid ethyl ester | |
| Identifiers | |
623-73-4  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 11692 |
| ECHA InfoCard | 100.009.828 |
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| Properties | |
| C4H6N2O2 | |
| Molar mass | 114.10 g/mol |
| Appearance | yellow oil |
| Density | 1.085 g/cm3 |
| Melting point | −22 °C (−8 °F; 251 K) |
| Boiling point | 140 to 141 °C (284 to 286 °F; 413 to 414 K) 720 mmHg |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Ethyl diazoacetate (N=N=CHC(O)OC2H5) is a diazo compound and a reagent in organic chemistry. It was discovered by Theodor Curtius in 1883.[3] The compound can be prepared by reaction of the ethyl ester of glycine with sodium nitrite and sodium acetate in water.
It is used in the cyclopropanation of alkenes.
Although the compound is hazardous it is used in chemical industry.[4] Procedures for safe industrial handling have been published [5]
Applications
Tranylcypromine, Trovafloxacin
References
- ↑ Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Org. Synth. 24: 56.; Coll. Vol., 3, p. 392
- ↑ "Ethyl diazoacetate". Sigma-Aldrich.
- ↑ Curtius, T. (1883). "Ueber die Einwirkung von salpetriger Säure auf salzsauren Glycocolläther" [On the reaction of nitrous acid with glycine ethyl ester hydrochloride]. Berichte der Deutschen Chemischen Gesellschaft. 16 (2): 2230–2231. doi:10.1002/cber.188301602136.
- ↑ Maas, G. (2009). "New Syntheses of Diazo Compounds". Angewandte Chemie International Edition. 48 (44): 8186–8195. doi:10.1002/anie.200902785.
- ↑ Clark, J. D.; Shah, A. S.; Peterson, J. C. (2002). "Understanding the large-scale chemistry of ethyl diazoacetate via reaction calorimetry". Thermochimica Acta. 392–393: 177–186. doi:10.1016/S0040-6031(02)00100-4.
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