Chemistry:Ethyl diazoacetate

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Ethyl diazoacetate[1][2]
Ethyl diazoacetate skeletal.png
Names
Preferred IUPAC name
Ethyl diazoacetate
Other names
Ethyl 2-diazoacetate
2-Diazoacetic acid ethyl ester
Identifiers
3D model (JSmol)
ChemSpider
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 GHS02: FlammableGHS07: HarmfulGHS08: Health hazardGHS01: Explosive
GHS Signal word Danger
H226, H240, H302, H315, H320, H351
P281, P305+351+338, P501
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 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.

Ethyl diazoacetate synthesis

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 5-HT2C agonist that is even superior to lorcaserin.

References

  1. ↑ Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Organic Syntheses 24: 56. http://www.orgsyn.org/demo.aspx?prep=cv3p0392. ; Collective Volume, 3, pp. 392 
  2. ↑ "Ethyl diazoacetate". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/fluka/33501?lang=en&region=US. 
  3. ↑ "Safety Data Sheet". 11 October 2018. 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". Berichte der Deutschen Chemischen Gesellschaft 16 (2): 2230–2231. doi:10.1002/cber.188301602136. https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692861;view=1up;seq=544. 
  5. ↑ Maas, G. (2009). "New Syntheses of Diazo Compounds". Angewandte Chemie International Edition 48 (44): 8186–8195. doi:10.1002/anie.200902785. PMID 19790217. 
  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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