Ethyl diazoacetate

Ethyl diazoacetate[1][2]
Names
	Preferred IUPAC name Ethyl diazoacetate
	Other names Ethyl 2-diazoacetate; 2-Diazoacetic acid ethyl ester
Identifiers
CAS Number	623-73-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	11692 ;
ECHA InfoCard	100.009.828
EC Number	210-810-8;
PubChem CID	12192;
UNII	N84B835FMR;
	InChI InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 Key: YVPJCJLMRRTDMQ-UHFFFAOYSA-N ; InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 Key: YVPJCJLMRRTDMQ-UHFFFAOYAC;
	SMILES CCOC(=O)C=[N+]=[N-];
Properties
Chemical formula	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]
Pictograms
Signal word	Danger
Hazard statements	H226, H240, H302, H315, H320, H351
Precautionary statements	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). verify (what is ?) 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.

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-HT_2C agonist that is even superior to lorcaserin.

References

Womack, E. B.; Nelson, A. B. (1944). "Ethyl Diazoacetate". Organic Syntheses. 24: 56.; Collective Volume, vol. 3, p. 392
"Ethyl diazoacetate". Sigma-Aldrich.
"Safety Data Sheet" (PDF). chemblink.com. 11 October 2018.
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.
Maas, G. (2009). "New Syntheses of Diazo Compounds". Angewandte Chemie International Edition. 48 (44): 8186–8195. doi:10.1002/anie.200902785. PMID 19790217.
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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[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.

[old-sigma-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. doi:10.1016/S0040-6031(02)00100-4.