Ethyl diazoacetate

Ethyl diazoacetate^[1][2]

Names
IUPAC name Ethyl diazoacetate
Other names 2-diazoacetic acid ethyl ester
Identifiers
CAS Number	623-73-4
ChemSpider	11692
Jmol interactive 3D	Image
InChI InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 Key: YVPJCJLMRRTDMQ-UHFFFAOYSA-N InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 Key: YVPJCJLMRRTDMQ-UHFFFAOYAC
SMILES CCOC(=O)C=[N+]=[N-]
Properties
Chemical formula	C4H6N2O2
Molar mass	114.10 g/mol
Appearance	yellow oil
Density	1.085 g/cm^3
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

1. Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Org. Synth. 24: 56.; Coll. Vol. 3, p. 392
2. "Ethyl diazoacetate". Sigma-Aldrich.
3. Curtius, T. (1883). "Ueber die Einwirkung von salpetriger Säure auf salzsauren Glycocolläther". Berichte der Deutschen Chemischen Gesellschaft 16 (2): 2230–2231. doi:10.1002/cber.188301602136.
4. Maas, G. (2009). "New Syntheses of Diazo Compounds". Angewandte Chemie International Edition 48 (44): 8186–8195. doi:10.1002/anie.200902785.
5. 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.