Ethyl diazoacetate

Ethyl diazoacetate
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
EC Number
  • 210-810-8
UNII
  • InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3 Y
    Key: YVPJCJLMRRTDMQ-UHFFFAOYSA-N Y
  • 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:
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).
Y verify (what is YN ?)
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. 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. Procedures for safe industrial handling have been published.

Another location where EDA was used is in the production of BI-4752, a invented 5-HT2C agonist that is even better than lorcaserin.

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