Ethyl diazoacetate

Last updated
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
ECHA InfoCard 100.009.828 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-810-8
PubChem CID
UNII
  • InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 Yes check.svgY
    Key: YVPJCJLMRRTDMQ-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearanceyellow 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]
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-explos.svg
Danger
H226, H240, H302, H315, H320, H351
P281, P305+P351+P338, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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 fuelInstability 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
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Synthesis of ethyl diazoacetate.png

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]

References

  1. ↑ Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Organic Syntheses . 24: 56; Collected Volumes, vol. 3, p. 392.
  2. ↑ "Ethyl diazoacetate". Sigma-Aldrich.
  3. ↑ "Safety Data Sheet" (PDF). chemblink.com. 11 October 2018.
  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. Bibcode:2002TcAc..392..177C. doi:10.1016/S0040-6031(02)00100-4.
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