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Dimethyl methylphosphonate is used as a catalyst and a reagent in organic synthesis for the conversion of esters to ketophosphonates. It is an additive for the synthesis of unsaturated polyester resin which has flame retardant high phosphorous and UV-cured epoxy acrylate. It finds application as hydraulic fluids as well.
The lithio-derivative reacts with esters to give ß-ketophosphonates, useful precursors of ɑß-unsaturated ketones by Horner-Wadsworth-Emmons olefination: J. Am. Chem. Soc., 88, 5654 (1966). An intramolecular version leads to cyclopentenones: Synth. Commun., 5, 1 (1975); Tetrahedron Lett., 22, 257 (1981). Dimethyl glutarate gives the 3-(phosphonatomethyl)cyclohexenone, olefination of which affords the corresponding 3-alkenylcycloalkenone. Dimethyl succinate also gives this reaction, but in lower yield; higher diesters give acyclic products: J. Org. Chem., 59, 1943 (1994):
See also Diethyl methylphosphonate, A14772 and Appendix 1.
Park, E. J.; Han, S. W.; Jeong, B.; Park, S. H.; Kim, Y. G.; Kim, Y. H.; Kim, Y. D. Effect of polydimethylsiloxane (PDMS) coating on TiO2-based MALDI matrix for dimethyl methylphosphonate (DMMP) analysis. Appl. Surf. Sci. 2015, 353, 342-349.
Yoo, R.; Cho, S.; Song, M. J.; Lee, W. Highly sensitive gas sensor based on Al-doped ZnO nanoparticles for detection of dimethyl methylphosphonate as a chemical warfare agent simulant. Sens. Actuators, B 2015, 221, 217-223.
Hazard Statements: H227-H319-H340-H361
Combustible liquid. Causes serious eye irritation. May cause genetic defects. Suspected of damaging fertility or the unborn child.
Precautionary Statements: P210u-P201-P280-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. 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.