Sarin synthesis

Li, Q., Hirata, Y., Piao, S., Minami, M. (2000). The byproducts generated during sarin-synthesis in the Tokyo sarin disaster induced inhibition of natural killer and cytotoxic T lymphocyte activity. Toxicology 146 209-20. 

Figure 4.10 is reprinted from Journal of Materials Research, Vol. 11, P D Mulpuri and V K Sarin, Synthesis of mullite coatings by chemical vapor deposition, pp. 1315-1324, 1996, with permission from Materials Research Society. 

The nerve agents are generally considered to be acute toxicants and their delayed effects have been relatively little investigated. Li et al. (1998) reported an increase in sister chromosome exchange (SCE) in the lymphocytes of victims of the Tokyo sarin disaster. Because of the probability that the victims were exposed to by-products of sarin synthesis, diisopropyl methylphospho-nate, diethyl methylphosphonate and isopropyl ethyl methylphosphonate, these were also studied. The frequency of SCE was determined in human lymphocytes exposed to these by-products all three compounds increased the frequency of SCE compared with controls. Sarin and soman... 

Li Q, Minami M, Clement JG et al. (1998). Elevated frequency of sister chromatid exchanges in lymphocytes of victims of the Tokyo sarin disaster and in experiments exposing lymphocytes to byproducts of sarin synthesis. Toxicol Lett, 98, 95-103. 

Ethylphosphonyl dichloride 1066-50-8 Organic synthesis Specific uses not identified see ethylphosphonous dichloride Ethyl sarin (GE) 2.10... 

VK Sarin, SBH Kent, JP Tam, RB Merrifield. Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. Anal Biochem 117, 147, 1981. 

VK Sarin, SBH Kent, RB Merrifield. Properties of swollen polymer networks. Solvation and swelling of peptide-containing resins in solid-phase peptide synthesis. JAm Chem Soc 102, 5463, 1980. 

Alkylphosphonochloridates may be used as starting materials for the synthesis of the corresponding alkylphosphonofluoridates. Two of these compounds, chlorosarin and chlorosoman (see Table 1), are placed on the CWC Schedule 1 list. The main peaks in the El mass spectrum of chlorosarin (MW 156) at mlz 115/117 (loss of C3H5) and mlz 141 (loss of CH3) are in accordance with the fragmentation pattern of sarin. The same analogy applies to chlorosoman (MW 198) with abundant ions at m/z 142/144 (loss of C4H8) and m/z 115/117 (loss of CsHn), and soman (10). 

Durst et al. (29) made microscale synthesis of several sarin analogues in autosampler vials and analyzed them directly with a gas chromato-graphy/infrared spectroscope/mass spectrometer (GC/IR/MS) instrument. Ninety different alkyl and cycloalkyl alcohols were used. They presented a couple of light-pipe IR spectra and a table of typical gas-phase frequencies (vp F, vp=0, pP methyl, 8S P methyi, vp 0 c) for 12 sarin-type chemicals. 

Other industrially important uses of P4O10 include the reactions with ethers, an example of which is the formation of triethyl phosphate via reaction with diethyl ether followed by pyrolysis. The product (which has a worldwide production of many thousands of tons per annum) finds use as ketene synthesis, a flame retardant, and a plasticizer within the plastics industry a less conventional use is as a simulant for the sarin when modeling situations involving the latter nerve agent. 

Typical production batches of nerve agents formerly intended for military use are mixtures of enantiomers obtained from nonchiral synthesis (Figure 50.1). Sarin, cyclosarin, tabun, and VX consist of mixtures of two enantiomers each of which differs in the chirality at the central phosphorus atom thus enabling rotation of linearly polarized light clockwise [P(+)-enantiomers] or anticlockwise [P(—)-enantiomers] (Figure 50.1). In contrast, chirality of soman appears more complex based on two chiral centers, which reside at the phosphorus atom, P(-f) and P(—), and additionally in the pinacolyl moiety, C(-f) and C( ). Hence, soman occurs in four stereoisomeric conformations as two pairs of diastereomers P(-E)C(+),... 

Seto, Y. (2001). The sarin gas attack in Japan and the related forensic investigation. Organization for the Prohibition of Chemical Weapons (http //www.opcw.org/synthesis/html/s6/ pl4prt.html). 

Letsinger, R. L., Zhang, G. R., Sun, D. K., Ikeuchi, T., and Sarin, P. S. (1989) Cholesteryl-conjugated oligonucleotides synthesis, properties, and activity as inhibitors of replication of human immunodeficiency vims in cell culture. Proc. Natl. Acad. Sci. USA 86, 6553-6556. 

The good swelling properties of a peptide resin not only determines its diffusion properties, and therefore the kinetics of a solid-phase reaction,P 9 but also are a requirement for ensuring a uniform distribution of the growing peptide chains throughout the polymeric support. This uniform distribution can actually be achieved, at least in favorable cases, as was shown by an elegant experiment performed by Sarin et al.t where Boc-PH]valine was incorporated into a peptide synthesis and autoradiographs of cross sections of peptide resin beads showed a completely uniform pattern. 

Chemistry Like tabun, sarin was first prepared (1938) by Schrader s group at LG. Farben. An early synthesis involved the use of methylphosphonic dichloride (CH3P(0)Cl2) as a starting material. An interesting route involves the reaction of a tetraalkoxysilane, (RO)4Si, as a source of the alkoxy fragment in GB (Black and Harrison, 1996a). 

Chemistry The synthesis of soman is similar to that of sarin. The major alteration is that pinacolyl alcohol replaces isopropanol. Soman hydrolyzes over a range of pHs, with pinacolyl methylpho-sphonate and fluoride ions being the initial products. Subsequent hydrolysis of pinacolyl methyl-phosphonate is similar to the aging process associated with GD poisoning (below) (Michel et al., 1967). 

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