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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.[4] The compound can be prepared by reaction of the ethyl ester of glycine with sodium nitrite and sodium acetate in water.

Ethyl diazoacetate[1][2]
Names
Preferred IUPAC name
Ethyl diazoacetate
Other names
Ethyl 2-diazoacetate
2-Diazoacetic acid ethyl ester
Identifiers
  • 623-73-4 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 11692 Y
ECHA InfoCard 100.009.828
EC Number
  • 210-810-8
  • 12192
UNII
  • N84B835FMR
  • 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:[3]
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 ?)

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-HT2C agonist that is even superior to lorcaserin.

References

  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.
  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.

ethyl, diazoacetate, oc2h5, diazo, compound, reagent, organic, chemistry, discovered, theodor, curtius, 1883, compound, prepared, reaction, ethyl, ester, glycine, with, sodium, nitrite, sodium, acetate, water, namespreferred, iupac, name, other, names, ethyl, . 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 1 2 NamesPreferred IUPAC name Ethyl diazoacetateOther names Ethyl 2 diazoacetate2 Diazoacetic acid ethyl esterIdentifiersCAS Number 623 73 4 Y3D model JSmol Interactive imageChemSpider 11692 YECHA InfoCard 100 009 828EC Number 210 810 8PubChem CID 12192UNII N84B835FMRInChI InChI 1S C4H6N2O2 c1 2 8 4 7 3 6 5 h3H 2H2 1H3 YKey YVPJCJLMRRTDMQ UHFFFAOYSA N YInChI 1 C4H6N2O2 c1 2 8 4 7 3 6 5 h3H 2H2 1H3Key YVPJCJLMRRTDMQ UHFFFAOYACSMILES CCOC O C N N PropertiesChemical formula C4H6N2O2Molar mass 114 10 g molAppearance yellow oilDensity 1 085 g cm3Melting point 22 C 8 F 251 K Boiling point 140 to 141 C 284 to 286 F 413 to 414 K 720 mmHgHazardsGHS labelling 3 PictogramsSignal word DangerHazard statements H226 H240 H302 H315 H320 H351Precautionary statements P281 P305 P351 P338 P501NFPA 704 fire diamond 220Safety data sheet SDS Ethyl diazoacetateExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N 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 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 HT2C agonist that is even superior to lorcaserin References Edit 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 Saure auf salzsauren Glycocollather 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 Retrieved from https en wikipedia org w index php title Ethyl diazoacetate amp oldid 1131234970, wikipedia, wiki, book, books, library,

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