Ethyl diazoacetate

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
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
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 codeNFPA 704 four-colored diamond
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

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.

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]

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. 1 2 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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