Ethyl diazoacetate

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.[4] The compound can be prepared by reaction of the ethyl ester of glycine with sodium nitrite and sodium acetate in water.

Ethyl diazoacetate[1][2]
Names
Preferred IUPAC name
Ethyl diazoacetate
Other names
Ethyl 2-diazoacetate
2-Diazoacetic acid ethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.828
EC Number
  • 210-810-8
UNII
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
Hazards
Safety data sheet Ethyl diazoacetate
GHS pictograms [3]
GHS Signal word Danger
H226, H240, H302, H315, H320, H351[3]
P281, P305+351+338, P501[3]
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
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

As a carbene precursor, it is used in the cyclopropanation of alkenes.

Although the compound is hazardous, it is used in chemical industry as a precursor to trovafloxacin.[5] Procedures for safe industrial handling have been published.[6]

Another location where EDA was used is in the production of BI-4752, a recently invented 5HT2C agonist that is even superior to lorcaserin.

References

  1. Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Organic Syntheses. 24: 56.; Collective Volume, 3, p. 392
  2. "Ethyl diazoacetate". Sigma-Aldrich.
  3. http://www.chemblink.com/MSDS/MSDSFiles/623-73-4_Sigma-Aldrich.pdf
  4. 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.
  5. Maas, G. (2009). "New Syntheses of Diazo Compounds". Angewandte Chemie International Edition. 48 (44): 8186–8195. doi:10.1002/anie.200902785.
  6. 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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