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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-H332-H335-H340-H360-H373
Combustible liquid. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation. May cause genetic defects. May damage fertility or the unborn child. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P235-P260-P264b-P271-P280i-P281-P304+P340-P305+P351+P338-P308+P313-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe 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 eye/face protection. Use personal protective equipment as required. 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. IF exposed or concerned: Get medical advice/attention. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant