Ethyl diazoacetate

Summary

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]
Ethyl diazoacetate skeletal.png
Names
Preferred IUPAC name
Ethyl diazoacetate
Other names
Ethyl 2-diazoacetate
2-Diazoacetic acid ethyl ester
Identifiers
  • 623-73-4 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 11692 checkY
ECHA InfoCard 100.009.828 Edit this at Wikidata
EC Number
  • 210-810-8
  • 12192
UNII
  • N84B835FMR
  • InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 checkY
    Key: YVPJCJLMRRTDMQ-UHFFFAOYSA-N checkY
  • InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3
    Key: YVPJCJLMRRTDMQ-UHFFFAOYAC
  • CCOC(=O)C=[N+]=[N-]
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
GHS labelling:[3]
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS01: Explosive
Danger
H226, H240, H302, H315, H320, H351
P281, P305+P351+P338, P501
NFPA 704 (fire diamond)
2
2
0
Safety data sheet (SDS) Ethyl diazoacetate
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 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.

ReferencesEdit

  1. ^ Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Organic Syntheses. 24: 56.; Collective Volume, vol. 3, p. 392
  2. ^ "Ethyl diazoacetate". Sigma-Aldrich.
  3. ^ http://www.chemblink.com/MSDS/MSDSFiles/623-73-4_Sigma-Aldrich.pdf[bare URL 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. 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.