ethyl diazoacetate

{{chembox

| Watchedfields = changed

| verifiedrevid = 422549176

| Reference = {{ OrgSynth |author1=Womack, E. B.|author2=Nelson, A. B. | title = Ethyl Diazoacetate | year = 1944 | volume = 24 | pages = 56 | collvol = 3 | collvolpages = 392 | prep = cv3p0392}}{{cite web | url = http://www.sigmaaldrich.com/catalog/product/fluka/33501?lang=en®ion=US | title = Ethyl diazoacetate | publisher = Sigma-Aldrich }}

| ImageFile = Ethyl diazoacetate skeletal.png

| PIN = Ethyl diazoacetate

| OtherNames = Ethyl 2-diazoacetate
2-Diazoacetic acid ethyl ester

|Section1={{Chembox Identifiers

| Abbreviations =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 11692

| InChIKey = YVPJCJLMRRTDMQ-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YVPJCJLMRRTDMQ-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 623-73-4

| EINECS = 210-810-8

| PubChem = 12192

| UNII = N84B835FMR

| SMILES = CCOC(=O)C=[N+]=[N-]

| InChI = 1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3

}}

|Section2={{Chembox Properties

| Formula = C₄H₆N₂O₂

| MolarMass = 114.10 g/mol

| Appearance = yellow oil

| Density = 1.085 g/cm³

| MeltingPtC = -22

| MeltingPt_notes =

| BoilingPtC = 140 to 141

| BoilingPt_notes = 720 mmHg

| Solubility =

| SolubleOther =

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.chemblink.com/MSDS/MSDSFiles/623-73-4_Sigma-Aldrich.pdf Ethyl diazoacetate]

| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}{{GHS01}}

| GHS_ref = {{cite web|url=http://www.chemblink.com/MSDS/MSDSFiles/623-73-4_Sigma-Aldrich.pdf|title=Safety Data Sheet|date= 11 October 2018|website=chemblink.com}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|240|302|315|320|351}}

| PPhrases = {{P-phrases|281|305+351+338|501}}

| FlashPtC =

| AutoignitionPtC =

| ExploLimits =

| NFPA-H = 2

| NFPA-F = 2

| NFPA-R = 0

}}

}}

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.{{ cite journal | author = Curtius, T. | title = Ueber die Einwirkung von salpetriger Säure auf salzsauren Glycocolläther |trans-title=On the reaction of nitrous acid with glycine ethyl ester hydrochloride | journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1883 | volume = 16 | issue = 2 | pages = 2230–2231 | url = https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692861;view=1up;seq=544 | doi = 10.1002/cber.188301602136}} The compound can be prepared by reaction of the ethyl ester of glycine with sodium nitrite and sodium acetate in water.

:Image: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.{{ cite journal | author = Maas, G. | title = New Syntheses of Diazo Compounds | journal = Angewandte Chemie International Edition | year = 2009 | volume = 48 | issue = 44 | pages = 8186–8195 | doi = 10.1002/anie.200902785 | pmid = 19790217 }} Procedures for safe industrial handling have been published.{{ cite journal |author1=Clark, J. D. |author2=Shah, A. S. |author3=Peterson, J. C. | title = Understanding the large-scale chemistry of ethyl diazoacetate via reaction calorimetry | journal = Thermochimica Acta | year = 2002 | volume = 392–393 | pages = 177–186 | doi = 10.1016/S0040-6031(02)00100-4|bibcode=2002TcAc..392..177C }}

Another location where EDA was used is in the production of BI-4752, a invented 5-HT_2C agonist that is even better than lorcaserin.