Ethyl diazoacetate

Ethyl diazoacetate[1][2]
IUPAC name

Ethyl diazoacetate
Other names

2-diazoacetic acid ethyl ester
Identifiers
CAS number 623-73-4 Y
ChemSpider 11692 Y
Jmol-3D images Image 1
Properties
Molecular formula C4H6N2O2
Molar mass 114.10 g/mol
Appearance yellow oil
Density 1.085 g/cm3
Melting point

- 22 °C, 251 K, -8 °F
Boiling point

140-141 °C, 272 K, -82 °F (720 mmHg)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

  1. ^ OrgSynth Vol. 3, p.392 Link.
  2. ^ SigmaAldrich.com
  3. ^ T. Curtius, Ber. Dtsch. Chem. Ges. 1883, 16, 2230–2231;
  4. ^ New Syntheses of Diazo Compounds Gerhard Maas Angew. Chem. Int. Ed. 2009, 48, 8186 – 8195 doi:10.1002/anie.200902785
  5. ^ Understanding the large-scale chemistry of ethyl diazoacetate via reaction calorimetry Pages 177-186 Jerry D. Clark, Ajit S. Shah, James C. Peterson Thermochimica Acta Volumes 392-393, 15 September 2002, Pages 177-186 doi:10.1016/S0040-6031(02)00100-4