Ethyl methylphosphonofluoridate

Interactions Between Organophosphorus Compounds and Soil Materials I. Adsorption of Ethyl-methylphosphonofluoridate by Clay and Organic Matter Preparations and by Soils," M. H. B. Hayes, P. R. Lundie and M. Stacey, Pestic. Sci., 3 (1972) 619-629. 

E.M. Jakubowski, L.S. Heykamp, H.D. Durst and S.A. Thomson, Preliminary studies in the formation of ethyl methylphosphonofluoridate from rat and human serum exposed to VX and treated with fluoride ion, Anal. Lett., 34, 727-737 (2001). 

A 1 4 mixture of tetraethoxysilane and methylphosphonic difluoride stirred at room temp, (the temp, rising to 33° over the first 50 min and to 70° over the following 5-6 min) - ethyl methylphosphonofluoridate. Y 81%. CAUTION the products are highly toxic acetylcholineesterase inhibitors. F.e.s. A.J. Muller, J. Org. Chem. 53, 3364-5 (1988). 

The catalytic degradation of the nerve agent VX (O-ethyl 5 -2-(diiso-propylamino)ethyl methylphosphonothioate, 622) by water-swelled polymer-supported ammonium fluorides (623), has been described by Zafrani et al. VX (622) was rapidly degraded to form the G-analogue (O-ethyl methylphosphonofluoridate, 625), which hydrolysed to the nontoxic EMPA (ethyl methylphosphonic acid, 624) (Scheme 153). ° ... 

Nerve agents are organophosphonate compounds. They contain phosphorus double-bonded to an oxygen atom and single-bonded to a carbon atom. GB is O-isopropyl methylphosphonofluoridate. VX is O-ethyl-S [2-(diisopropyl amino) ethyl]-methylphospho-nothiolate. 

Sarin, TrUon 46, Isopropylmethylphosphonofluoridate, Isopropylmethylphosphoryl fluoride Sarin-ethyl, Sarin-II, Isopropylethylphosphonofluoridate, Isopropylethylphosphoryl fluoride Sarin-ethyl, Sarin-11, Isopropylethylphosphonofluoridate, Isopropylethylphosphoryl fluoride Sarin-isopropyl, Sarin-111, Isopropyl-2-propylphosphonofluoridate, Isopropoxy-2-propylphosphoryl fluoride Sarin-isopropyl, Sarin-111, Isopropyl-2-propylphosphonofluoridate, Isopropoxy-2-propylphosphoryl fluoride Soman, TrUon, Pinacolyl methylphosphonofluoridate, Methylphosphonofluoridic acid,... 

Methylphosphonofluoridic acid 1,2,2-tri-methylpropyl ester Methytlphosphonothioic acid S-[2-[bis(l-methylethyl)amino]ethyl] O-ethyl ester Methylthiophosphorusfluoridic acid 1,3-tri-methylpropyl ester Monomethyl cyclohexanepentanitrate Mustard gas II, 2,2 -Dichlorodipropryl sulfide, Bis(beta-chloropropryl) sulfide Mustard gas NC... 

GBE, 12, 40, 66, 92, 114, 118, 167. See also Sarin-ethyl, sarin-II, isopropylethylphosphonofluoridate, isopropylethylphosphoryl fluoride GBI, 12, 40, 66, 93, 114, 118, 168. See also Sarin-isopropyl, sarin-III, isopropoxy-2-propylphosphonofluoridate, isoproxy-2-propylphosphoryl fluoride GD, 13, 40, 66, 93, 115, 117-119, 166-167, 179, 182, 186. See also Soman, trilon, pinacolyl methylphosphonofluoridate, methylphosphonofluoridate, methylphosphonofluoridic acid, 1,2,2-tri-methylpropyl ester... 

The G-nerve agents include GA (tabun, ethyl A,A-dimethyl-phosphoramidocyanidate), GB (sarin, isopropyl-methylphosphonofluoridate), GD (soman, 1,2,2-tri-methylpropyl methylphosphonofluoridate), and VX (o-ethyl 5-[2-(diisopropylamino)ethyl] methylphosphonothiolate). The V-type nerve agents are several orders of magnitude less volatile than the G-type agents and act primarily as a liquid via the percutaneous route for example, VX is several orders of magnitude more lethal percutaneously than sarin (Reutter, 1999). 

METHYL PHOSPHONIC DICHLORIDE see MOB399 METHYLPHOSPHONOFLUORIDIC ACID ISOPROPYL ESTER see IPXOOO METHYLPHOSPHONOFLUORIDIC ACID-1-METHYLETHYL ESTER see IPXOOO METHYLPHOSPHONOTHIOIC ACID-S-(2-(BIS(METHYLETHYL)AAaNO)ETHYL)o-ETHYL ESTER see EIGOOO... 

Nerve agents Also known as anticholinesterase agents, are chemical compounds that inhibit the ability of cholinesterase to hydrolyze acetylcholine, which is essential to mediation of neurotransmitter function in nerve impulses. Nerve agents include VX (0-ethyl S-(2-dusopropylaminoethyl) methylphospho-nothioate) and the G-series agents tabun (GA)-dimethylphosphoramido-cyanidate, sarin G -isopropyl methylphosphonofluoridate and soman (GD)-Pinacolyl methyl phosphonofluoridate. 

Interpretation and understanding of the toxicokinetics of nerve agents would not be possible without taking into consideration that these agents consist of mixtures of stereoisomers, which are often extremely different in their toxicokinetic and toxico-dynamic properties. A common feature of these agents is the presence of chirality (asymmetry) around the phosphorus atom. Therefore, O-isopropyl methylphos-phonofluoridate (sarin) and 0-ethyl S-(2-diisopropylaminoethyl) methylphospho-nothioate (VX) consist of equal amounts of stereoisomers, denoted as (-1-)- and (-)-sarin and (-1 )- and (-)-VX, respectively. In the case of 0-1,2,2-trimethylpropyl methylphosphonofluoridate (soman), an additional chiral center resides in the 1,2,2-methylpropyl (pinacolyl) moiety, leading to the presence of four stereoisomers. Synthetic soman, i.e., a mixture of the four stereoisomers, is denoted as C( )P( )-soman, whereas the individual four stereoisomers are denoted as C(+)P(-l-), C(-H)P(-), C(-)P(+), and C(-)P( ), in which C stands for chirality in the pinacolyl moiety and P for chirality around phosphorus. The enantiomeric pairs [C(-r)P(+) + C(-)P( )] and [C(+)P(-) -l- C(-)P(+)] are present in synthetic... 

Nerve agents are organophosphonate compounds they contain phosphorus double-bonded to an oxygen atom and single-bonded to a carbon atom. GB is O-isopropyl methylphosphonofluoridate. VX is 0-ethyl-S[2-(diisopropyl amino) ethyl]-methylphosphonothiolate. Bis(2-chloroethyl) sulfide is the proper chemical name for mustard agent HD and HT (a thickened form). Mustard gas, sulfur mustard, and yperite have also been used for this agent. The term mustard gas is often used, but the chemical is a liquid at ambient temperature. 

Solvent-free hydrolysis of the warfare agents VX (<9-ethyl S -2-(diiso-propylamino)ethyl methylphosphonothioate) (410), GB (O-isopropyl methylphosphonofluoridate or sarin) (414), in the presence of various alumina-supported fluoride reagents such as KF/AI2O3, AgF/KF/Al203 and KF/AI2O3 has been described by Zafrani and co-workers. " While (414) reacted instantaneously with these solid supports to yield the non-toxic product z-propyl methylphosphonic acid (415), the less reactive (410) gave... 

The common nerve agents that are encountered in chemical warfare agent-filled munitions are isopropyl methylphosphonofluoridate (GB or sarin), pinacolyl methylphosphonofluoridate (GD or soman), and O-ethyl, S-(N,N-diisopropyl)aminoethyl methylphosphonothio-late (VX). These compounds are acutely toxic, with median lethal dose (LD50) values on the order of tens of micrograms per kilogram for humans, which make detection of trace quantities extremely important, and also render them difficult to handle in conducting analytical experiments. Given this limitation, the small size and ease of operation are favorable attributes of the... 

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