Dimethyl fluorophosphate

Dimethyl fluorophosphate is a strong acetylcholinesterase inhibitor. It is not used as a military poison. Its toxic actions are similar to those of DFP the poisoning effects may be slightly greater than those of DFP. 

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

Other chemicals which inhibit milk lipase include hydrogen peroxide, animal cephalin, sodium arsenite, diisopropyl fluorophosphate, 2,4 din-itro-l-fluorobenzene, p-hydroxymercuribenzoate, potassium dichromate, lauryl dimethyl benzyl ammonium chloride, aureomycin, penicillin, streptomycin, and terramycin (Schwartz 1974). 

Methyl-2-diphenylphosphino-3-(l -isoquinolyl)indole with pallada-cycle derived from dimethyl-1-naphthyl ethylamine and potassium hexa-fluorophosphate yields chelate 310 (97T4035). With [(r)3-PhCH = CH = CHPh)Pd( j.-Cl)]2, allyl 311 follows in the presence of silver tetrafluor-oborate. Addition of ligands 312 (R = R1 = H, Me) to [(r 3-PhCHCHCHPh)Pd (Cl) ]2 under conditions of allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate leads to the formation of P,N-chelates 313 (R = R1 = H, Me), the active species of the catalytic reaction (00T(A)4753). 

Substituted imidazole 1-oxides 263 upon treatment with dimethyl or diethyl sulfate furnish l-alkoxy-3-subtituted imidazolium salts 283 that were converted to the tetrafluoroborate 283 (A- = BF4 ) or hexafluorophos-phates 283 (A = PF6-) by treatment with sodium tetrafluoroborate or hexa-fluorophosphate (2007ZN(A)295). The tetrafluoroborates 283 (A = BF4 ) reacted with cyanide ion to give 2-cyanoimidazoles 285 (1975JCS(P1)275). The reaction probably follows a mechanism similar to that suggested to be operative in the pyrazole series encompassing O-alkylation succeeded by nucleophilic addition and elimination of methanol (Scheme 85). 

Diisopropyl fluorophosphate Dimethyl sulfate and related compounds Doxorubicin and daunorubicin Drugs containing hydrazine and triazene groups... 

DMF = dimethylfonnamide DMSO = dimethyl sulfoxide PC = propylene carbonate, THE = tetrahydrofuran. HFP= 1.1,1,3,3,3-hexafluoro-2-propanol THAB = tetrahexylammonium benzoate TBAPFf, = tetrabutylammonium hexa-fluorophosphate. 

PdF12N4P2Cl2Hjo, Palladium(ll), [W,W -bis[2-(di-methylaminoJethyll-W.A/ -dimethyl-1,2-ethanediamine]-, bis(hexa-fluorophosphate), 21 133... 

FtPjRuCwHn. Ruthenium(ll), (tf-cyclo-pentadienyl)(phenylvinylene)bis-(triphenylphosphine)-, hexa-fluorophosphate(l -), 21 80 FuFehyCaHn, Iron(U), bis(acetonitrile) (2,9-dimethyl-3,10-diphenyl-1,4,8,11 -tetraaza-cyclotetradeca-1,3,8,10-tetraene)-, bis[hexafluorophosphate(l —)], 22 108 F,2Fe2N2P2S2C, H36, lron(2 + ),... 

Phosphorodithioic acid, mixed 0,0-bis (isobutyl and pentyl) esters, zinc salt. See Zinc dialkyl dithiophosphate Phosphorofluoridic acid, calcium salt. See Calcium monofluorophosphate Phosphorofluoridic acid, disodium salt. See Sodium fluorophosphate (Na2P03p) Phosphorofluoridic acid, monoammonium salt. See Ammonium monofluorophosphate Phosphorofluoridic acid, potassium salt. See Potassium monofluorophosphate Phosphorothioic acid. See Diazinon Phosphorothioic acid, S-((6-chloro-2-oxooxazxolo(4,5-b) pyridin-3(2H)-yl)methyl) 0,0-dimethyl ester. See Azamethiphos, Phosphorothioic acid, 0-(2,5-dichloro-4-iodophenyl) 0,0-dimethyl ester. See lodofenphos... 

Benzyl chloride o-Chloroaniline 2-Chlorophenol Copper Maleic anhydride Quinone Sodium fluorophosphate (Na2POsF) 2,3-Xylenol fungicide, adhesives Diiodomethyl tolylsulfone 3,5-Dimethyl tetrahydro-2-H,1,3,5-thiadiazone-2-thione Hexahydro-1,3,5-triethyl-s-triazine lodopropynyl butylcarbamate Sodium p-chloro-m-cresol... 

Precursors, TMOS (tetramethyl orthojsilicate) and MTMS (methyltri-methoxysilane), were purchased from Aldrich Chemical Company (Milwaukee, WI). Diisopropyl fluorophosphates (DFP), l,3-bis(trishydroxymethylmethyl-amino) propane (BTP), D-fructose, polyethylene glycol (PEG, MW 400), hydrochloric acid (HCl), dimethyl formamide (DMF), acetone, methanol, and hexane were purchased from Sigma Chemical Company (St. Louis, MO). Sodium fluoride was purchased from Fisher Scientific (Fair Lawn, NJ). Organophosphate acid anhydrolase (OPAA, EC 3.1.8.2) was purified and provided by Dr. Tu-chen Cheng (U.S. Army). All chemicals and reagents were used as received. 

Finally, the development of the chemistry of hexacoordinated compounds has been mainly limited to the synthesis and modification of diverse perfluoroallqrl fluorophosphates. This was achieved by oxidative addition of fluorinated amines or diamines to fluorinated phosphanes. On the other hand, the modification of the perfluoroallyl fluorophos-phate anion was accessed by reactions of hexacoordinated DMAP-phos-phorane adduct with selected Bronsted acids. Additionally, it has been demonstrated that hexacoordinated transition states and intermediates may participate in the synthesis of 3,3-dimethyl-l-bis(o-phenylenedio3y)-X, -phosphanyl-2-trimethylsilo y-l-phosphabut-l-ene. 

In the second paper, the non-hindered Arduengo carbene PF5 adduct (56) was prepared by thermolysis of 1,3-dimethyl-lff-imidazolium hexa-fluorophosphate (57) under reduced pressure. This observation... 

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