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Triethyl 2-phosphonopropionate is used as a reactant in intramolecular conjugate addition for the synthesis of floresolide B, enantioselective synthesis of spiroindane di-methyl acetic acid and in stereo selective intramolecular Diels-Alder reactions. It plays an important role in Horner-Wadsworth-Emmons reactions and chemoenzymatic one-pot synthesis of gamma-butyrolactones. It is also used in the preparation of 3-furyl-2-methyl-acrylic acid ethyl ester by reacting with furfural.
Wadsworth-Emmons precursor of methacrylic esters (see Triethyl phosphonoacetate, A14120 and Appendix 1). Lithiation followed by acylation with perfluoroalkanoic anhydrides gives a perfluoroacyl intermediate which, with an organolithium reagent, leads stereoselectively to a trifluoroalkylated ɑß-unsaturated ester: J. Fluorine Chem., 89, 141 (1998):
Sharpe, M. A.; Han, J.; Baskin, A. M.; Baskin, D. S. Design and Synthesis of a MAO-B-Selectively Activated Prodrug Based on MPTP: A Mitochondria-Targeting Chemotherapeutic Agent for Treatment of Human Malignant Gliomas. ChemMedChem 2015, 10 (4), 621-628.
Shouksmith, A. E.; Evans, L. E.; Tweddle, D. A.; Miller, D. C.; Willmore, E.; Newell, D. R.; Golding, B. T.; Griffin, R. J. Synthesis and Activity of Putative Small-molecule Inhibitors of the F-box Protein SKP2. Aust. J. Chem. 2015, 68 (4), 660-679.
Hazard Statements: H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P235-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant