Dimethyl methylphosphonates

Eyrol 51 is a water-soluble Hquid containing about 21% phosphoms. It is made by a multistep process from dimethyl methylphosphonate, phosphoms pentoxide, and ethylene oxide. The end groups are principally primary hydroxyl and the compound can thus be incorporated chemically into aminoplasts, phenoHc resins, and polyurethanes. Eyrol 51, or 58 if diluted with a small amount of isopropanol, is used along with amino resins to produce a flame-retardant resin finish on paper used for automotive air filters, or for backcoating of upholstery fabric to pass the British or California flammabiHty standards. 

Oligomeric Vinylphosphonate. A water-soluble oligomer, Fyrol 76 [41222-33-7] is produced by reaction of bis(2-chloroethyl) vinylphosphonate and dimethyl methylphosphonate with elimination of all the chlorine as methyl chloride (127,128). This Hquid, containing 22.5% P, is curable by free-radical initiation, on cotton or other fabrics. Nitrogen components, such as A/-methylolacrylamide or methylolmelamines, are usually included in the finish, which can be durable to multiple launderings (129,130). 

Ironically, the reactor was used to produce Antiblaze 19, a flame retardant used in textiles and polyurethane foam. Antiblaze 19 is a cyclic phosphorate ester produced from a mixture of trimethyl phosphite, dimethyl methylphosphonate (DMMP), and trimethyl phosphate (TMOP). The final product is not considered flammable, but trimethyl phosphite is moisture sensitive and flammable, with a flash point of about 27 C. 

Fasano R, Randel M, Sadowski L, et al. 1982. Analytical methods development for dimethyl methylphosphonate, diisopropyl methylphosphonate, and trimethyl phosphate. Cambridge, MA Arthur D. Little, Inc. NTIS No. AD-A120-863. 

The dimethyl methylphosphonate (XI) can also be readily prepared by the Arbusov rearrangement of trimethyl phosphite 3... 

Antiblaze 19, a phosphonate ester and flame retardant used in textiles and polyurethane foam manufactured from trimethyl phosphite, dimethyl methylphosphonate, and trimethyl phosphate. 

Nolan and co-workers have extended the scope of transesterification reactions to include phosphonate esters as phosphorylating agents [137]. In this publication the authors use dimethyl methylphosphonate 273 and benzyl alcohol with a variety of imidazolylidene carbenes (Table 23). The nse of molecnlar sieves to absorb methanol leads to increased conversion however, longer reaction times lead to decreased... 

Toxicology. Dimethyl methylphosphonate (DMMP) administered to male rats is a reproductive toxicant and carcinogen. Effects in humans are unknown. 

DMMP was not mutagenic in Salmonella assays. An ACGIH threshold limit value (TLV) has not been established for dimethyl methylphosphonate. 

National Toxicology Program Toxicology and Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice, pp 1-64. NTP TR 323, NIH Pub 87-2579,... 

Dunnick JK, Gupta BN, Harris MW, et al Reproductive toxicity of dimethyl methylphosphonate (DMMP) in the male Fischer 344 rat. Toxicol Appl Pharmacol 72 379-387, 1984... 

Chapin RE, Dutton SL, Ross MD, et al Development of reproductive tract lesions in male F344 rats after treatment with dimethyl methylphosphonate. Exp Mol Pathol 41 126-140, 1984... 

Dunnick JK, Eustis SL, Haseman JK Development of kidney tumors in the male F344/N rat after treatment with dimethyl methylphosphonate. Fundam Appl Toxicol 11 91-99,... 

Dimethyl methylphosphonate (DMMP) A dual-use precursor substance, usable for sarin production. 

Diethylamidoethoxyphosphoryl cyanide, 12 Diimine, 7, 35, 61, 88, 112, 176, 204 Diimine,N,N -bis-isopropyiethylenediimine, 7 Diisopropylamine trinatrate, 7, 89 DIM, 7, 35, 88, 112, 176. See also Diimine,NjAT-bis-isopropylethylenediimine Dimethobromide 1/2 hydrate, 5 Dimethobromide monohydrate, 5 Dimethyl methylphosphonate, 181 Dimethylamidoethoxyphosphorul fluoride-hydrochloride, 11... 

Figure 1 Structures of chemical warfare agents (sarin and soman), simulants (dimethyl methylphosphonate and diisoproyl fluorophosphate), and pesticides (paratliion and diazinon).

NMR has been used to study ligand exchange in non-coordinating solvents for a series of Be(C104)2-4L (L = trimethyl phosphate, DMSO, DMA, DMF, NMA, 1,1,3,3-tetramethylurea, dimethyl methylphosphonate and dimethyl phenylphosphonate) complexes. 3H NMR studies show that the mode of activation for exchange on beryllium varies from dissociative to associative depending upon L and the nature of the non-coordinating solvent.127 128... 

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