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Ethyl diazoacetate

Chemical compound From Wikipedia, the free encyclopedia

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 synthesis
Quick facts Names, Identifiers ...
Ethyl diazoacetate[1][2]
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 Edit this at Wikidata
EC Number
  • 210-810-8
UNII
  • 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]
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GHS02: Flammable
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GHS07: Exclamation mark
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GHS08: Health hazard
‹ The template below (GHS exploding bomb) is being considered for merging with GHS pictogram. See templates for discussion to help reach a consensus. ›
GHS01: Explosive
Danger
H226, H240, H302, H315, H320, H351
P281, P305+P351+P338, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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).
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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]

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