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Ethyl malonyl chloride is used in the syntheses of methanofullerodendimers and 3-pyrrolin-2-ones. It plays a vital role in the preparation of 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks. It is a versatile acylating agent for propargyl alcohols, hydrazines and amines.
Useful synthetic building block, e.g. in an oxazole synthesis: J. Med. Chem., 36, 3871 (1993):
Formation of amides has been used in the syntheses of 1,2,4-triazine-3,6-diones, and of a vicinal tricarbonyl amide derivative of L-phenylalanine: J. Org. Chem., 60, 5992 (1995); 61, 1872 (1996).
Yang, Z.; Li, S.; Zhang, Z.; Xu, J. Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines. Org. Biomol. Chem. 2014, 12 (48), 9822-9830.
Hayat, F.; Kang, L.; Lee, C. Y.; Shin, D. Synthesis of arylnaphthalene lignan lactone using benzoin condensation, intramolecular thermal cyclization and Suzuki coupling. Tetrahedron 2015, 71 (19), 2945-2950.
Hazard Statements: H227-H314-H318
Combustible liquid. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210u-P260u-P303+P361+P353-P305+P351+P338-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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.