Ethyl diazoacetate

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Ethyl diazoacetate[1][2]
Ethyl diazoacetate.png
IUPAC name
Ethyl diazoacetate
Other names
2-diazoacetic acid ethyl ester
623-73-4 YesY
ChemSpider 11692 YesY
Jmol-3D images Image
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 °C (284 °F; 413 K) 720 mmHg
Except where noted otherwise, data is 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.

Ethyl diazoacetate synthesis

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]


  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.