Ethyl diazoacetate
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.
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Preferred IUPAC name
Ethyl diazoacetate | |
Other names
Ethyl 2-diazoacetate 2-Diazoacetic acid ethyl ester | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.009.828 |
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PubChem CID |
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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
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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).
Infobox references |
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 recently invented 5-HT2C agonist that is even superior to lorcaserin.
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