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Diethyl oxalate is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates. It is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics. It is involved in the transesterification reaction with phenol to get dipheny oxalate. It is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives. Further, it is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine. In addition to this, it is utilized in the microemulsion synthesis of zinc oxide nanoparticles.
Base-promoted condensation with ketones, esters, nitriles, etc. yields ɑ-ethoxalyl derivatives, which with aldehydes, e.g. formaldehyde, yield ɑß-unsaturated compounds: J. Org. Chem., 42, 1180 (1977). Condensation with the activated methyl group of o-nitrotoluenes can lead to indole-2-carboxylic acid ethyl ester: Org. Synth. Coll., 5, 567 (1973), or to o-nitrophenylacetic acids which can be converted to indole-2-acetic acid esters: Org. Synth. Coll., 9, 601 (1998).
With the benzylic phosphoranes, gives stereoselectively (Z)-3-aryl-2-ethoxyacrylates: Synthesis, 958 (1989).
Reaction with Grignard reagents at low temperatures gives ɑ-keto esters: Synth. Commun., 11, 943 (1981); Org. Prep. Proced. Int., 21, 501 (1989). Similarly, vinyl Grignards give 2-oxo-3-alkenoic acids: Synthesis, 564 (1988).
Ding, J.; Zhang, J.; Zhang, C.; Liu, K.; Xiao, H.; Kong, F.; Chen, J. Hydrogenation of diethyl oxalate over Cu/SiO2 catalyst with enhanced activity and stability: Contribution of the spatial restriction by varied pores of support. Appl. Catal., A 2015, 508, 68-79.
Afrooz, M.; Dehghani, H. First application of diethyl oxalate as efficient additive in high performance dye-sensitized solar cells based on iodide/triiodide electrolyte. Electrochim. Acta 2015, 174, 521-531.
Gefahrenhinweise (EU): H227-H302-H319
Combustible liquid. Harmful if swallowed. Causes serious eye irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.