Chlorosoman
Chemical compound
From Wikipedia, the free encyclopedia
Chlorosoman is a chlorine analog of soman. It is a highly toxic organophosphorus compound and is used as the precursor substance for soman nerve agent.[2] Its physical properties are estimated. Soman is insoluble in water, with a boiling point of 223 °C and a melting point of -27 °C. Chlorosoman is at least 2.5 times less toxic than soman.[3]
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| Names | |
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| Preferred IUPAC name
3,3-Dimethylbutan-2-yl methylphosphonochloridate | |
| Other names
Pinacolyl methylphosphonochloridate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C7H16ClO2P | |
| Molar mass | 198.63 g·mol−1 |
| 1,030 mg/L[1] | |
| Vapor pressure | 0.207 mm Hg[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The chlorosoman (ClG) series of compounds is used more as a precursor to highly toxic compounds. For example, soman is a precursor to EA-2613 and EA-3209.
Synthesis
ClG follows the same synthetic route as soman, with fluoridation being omitted. Chlorosoman is prepared by the Finkelstein reaction between a solution of sodium chloride in DMF and soman.[4] A fluoride substitution is hypothetically made by the metathetic reaction between soman, anhydrous aluminum chloride, and sodium chloride in a suitable solvent, precipitating sodium hexafluoroaluminate.
- 6 CH3P(O)FOCH3CHC(CH3)3 + AlCl3 + 3 NaCl → 6 CH3P(O)ClOCH3CHC(CH3)3 + Na3AlF6↓