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Diethyl acetylenedicarboxylate is used as a protein cross-linker. It is also used in the synthesis of 3,4,5-trisubstituted 2(5H)-furanone derivatives, highly functionalized thiazolidinone derivatives, novel cyclic peroxide glucosides and 4,11-dimesitylbisanthene, soluble bisanthene derivative, via Diels-Alder reaction.
YW Guo; YL Shi; HB Li; M Shi. Reactions of salicyl N-tosylimines or salicylaldehydes with diethyl acetylenedicarboxylate for the synthesis of highly functionalized chromenes.Tetrahedron. 2006, 16 5875-5882.
Alan R. Katritzky; Jiangchao Yao; Weiliang Bao; Ming Qi; and Peter J. Steel. 2-Benzotriazolylaziridines and Their Reactions with Diethyl Acetylenedicarboxylate.J. Org. Chem. 1999, 64 (2), 346-350.
For reactions of acetylenedicarboxylic esters, see Dimethyl acetylenedicarboxylate, A11437.
Reaction with enamines leads to 2(1H)-pyridones: Synthesis, 371 (1992).
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.