Ethyl diazoacetate

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Ethyl diazoacetate[1][2]
Ethyl diazoacetate.png
CAS number 623-73-4 YesY
ChemSpider 11692 YesY
Jmol-3D images Image 1
Molecular formula 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 noted otherwise, 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.

Ethyl diazoacetate synthesis

It is used in the cyclopropanation of alkenes;

For example, the important medication tranylcypromine is made by reaction of EDAA with styrene as the first step.

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: 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.