Diethyl oxalate

Diethyl oxalate is an organic compound with the formula (CO2CH2CH3)2. It is the diethyl ester of oxalic acid. Diethyl oxalate is a colorless liquid. It is very similar to dimethyl oxalate but is a liquid at room temperature and has lower solubility in water. Both compounds are reagents in the synthesis of more complex compounds.

Diethyl oxalate
Names
Other names
ethyl oxalate
Identifiers
  • 95-92-1
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL3183226
ChemSpider
  • 6998
ECHA InfoCard 100.002.241
EC Number
  • 202-464-1
  • 7268
UNII
  • 860M3ZWF6J
UN number 2525
  • DTXSID2044472
  • InChI=1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3
    Key: WYACBZDAHNBPPB-UHFFFAOYSA-N
  • CCOC(=O)C(=O)OCC
Properties
C6H10O4
Molar mass 146.142 g·mol−1
Appearance colorless liquid
Density 1.0785 g/cm3
Melting point −38.5 °C (−37.3 °F; 234.7 K)
Boiling point 186 °C (367 °F; 459 K)
Hazards
GHS labelling:[1]
Signal word
Warning
H302, H319
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

Diethyl oxalate can be obtained by esterification of oxalic acid with ethanol using sulfuric acid as a catalyst. A procedure for the closely related dimethyl oxalate is available:

2 CH3CH2OH + (CO2H)2 → (CO2CH2CH3)2 + 2 H2O

Reactions

Diethyl oxalate participates in many condensation reactions, usually to produce esters.

Diethyl oxalate is often used to prepare heterocycles. It is for example a precursor to 3,4-ethylenedioxythiophene. With urea, it condenses to give parabanic acid.

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