Methylphosphonic acid, dimethyl ester

SYNS Di LMP METHYLPHOSPHONIC ACID DIMETHYL ESTER NCI-C56762... 

METHYI- PHOSPHATE see TMD250 METHYL PHOSPHITE see TAIDSOO METHYL PHOSPHONATE see DSG600 METHYLPHOSPHONIC ACID DIMETHYL ESTER see DSR400... 

Methylphosphonic Acid Dimethyl Ester A223 Precursor 128... 

Methylphosphonic acid, dimethyl ester. See Dimethyl methylphosphonate Methylphosphonic acid, (5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl methyl ester... 

Bellstein Handbook Reference) AI3-08678 BRN 0878263 CCRIS 876 DImethoxymethyl-phosphIne oxide Dimethyl methanephosphonate Di-methyl methylphosphonate DMMP EINECS 212-062-3 Fyrol DMMP HSDB 2590 Methyl phosphonic acid, dimethyl ester NCI-C54762 NSC 62240 Phosphonic add, methyl-, dimethyl ester Pyrol dmmp. Flame retardant for applications where high phosphorus content, good solvency, and low viscosity are desired lowers viscosity of epoxy resins and unsaturated polyesters filled with hydrated alumina oxide. Liquid bp = 181 , bp20 = 79.6" d ° = 1.4099 Am = 217 nm (e = 13, EtOH) soluble in H2O, Et20, EtOH LDsO (rat orl) > 5000 mg/kg. Akzo Chemie. 

Verwej et al. [175] have described a procedure for the determination of PH3-containing insecticides in surface water. In this procedure the insecticide is hydrolysed to methylphosphonic acid, and the acid is concentrated by anion exchange and converted to the dimethyl ester. After clean-up on a microsilica gel column the ester is analysed by gas chromatography using a thermionic phosphorus-specific detector. Detection limit is lnmol L 1. 

The methyl ester easily undergoes spontaneous isomerization to the dimethyl ester of methylphosphonic acid ... 

A relatively general procedure for the preparation of dialkyl 2-oxoalkylphosphonates by direct acylation of dialkyl 1-lithioalkylphosphonates has been introduced by Corey and Kwiatkowski in 1966. The use of phosphonate carbanions as nucleophiles in reaction with carboxylic esters avoids the problems associated with the Michaelis-Arbuzov reaction. The reaction sequence is initiated by the addition at low temperature of dimethyl 1-lithiomethylphosphonate (2 eq and frequently more) to a carboxylic ester (1 eq) to give the transient lithium phosphonoenolate. The dimethyl methylphosphonate, being readily available and easy to eliminate, is the most frequently used phosphonate, but other phosphonates such as diethyl and diisopropyl methylphosphonates can be used. When the resulting enolate is treated with acid, dimethyl 2-oxoalkylphosphonate is produced in moderate to good yields (45-95%, Scheme 7.20). The reaction has been achieved with... 

The alkyl methylphosphonic acids are polar and involatile and must be derivatized before analysis by gas chromatography. The simplest derivatization involves conversion into the methyl esters using diazomethane , or trimethylphenylammonium hydroxide in the hot injection port. However, the GC properties of the methyl esters, particularly dimethyl methylphosphonate, are not ideal and may give rise to poor peak shapes at low concentrations. Alternative derivatives are the trimethylsilyl or err-butyldimethylsi-jyji 14,133 latter are more stable than the trimethylsilyl esters and provide good... 

Phosphonic acid, methyl-, dimethyl ester. See Dimethyl methylphosphonate Phosphonic acid, methyl-, (5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl methyl ester, p-oxide. See Methylphosphonic acid, (5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl methyl ester Phosphonic acid, methyl (5-methyl-2-methyl-1,3,2-dioxaphosphorinan-5-y) ester,P,P -dioxide. See Methylphosphonic acid, bis [(5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl] ester Phosphonic acid, [nitriliotris (methylene)] tris-, sodium salt. See Sodium nitrilotris (methylene phosphate)... 

Phosphite esters, P(OR)3, are well known to inorganic chemists as transition-metal ligands. Trimethyl phosphite, however, is particularly reactive and spontaneously rearranges to the dimethyl ester of methylphosphonic acid ... 

The third most commonly used class of flame-retardants is phosphorus-containing compounds such as phosphoric acid esters, diphenyl cre-sylphosphate, dimethyl methylphosphonate, and dibutyl dihydroxyethyl diphosphate. They have good flame-retarding performance and are effective in small amounts. They are, however, expensive and have low hydrolysis stability. 

Commercially available dimethyl cyclopropylmalonate 30 was converted to mono ester 31 by careful saponification using sodium hydroxide. Coupling with l-amino-2-hexanol afforded the hydroxyamide 32 which was oxidized to ketone 33 under Swern conditions. Condensation to oxazole 34 was effectively achieved by utilizing a two-phase system consisting of dichloromethane and sulfuric acid. Reaction with deprotonated dimethyl methylphosphonate gave the 0-ketophosphonate 35 in an excellent overall yield. 

For the preparation of prostacyclin derivative ([3- " C]nonyl)SM-10902 1821. halo-decarboxylation of (35)-3-methylheptanoic acid 1781 gave key intermediate 79. Grignard reagent preparation, carboxylation with " COj, esterification and subsequent reaction of the resulting ethyl ester with lithiated dimethyl methylphosphonate afforded ketophos-phonate SI in 70% overall radiochemical yield. Homer—Wadsworth—Emmons reaction with the corresponding aldehyde derivative and reduction of the resulting a,/3-unsaturated ketone converted 81 into 82". ... 

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