Chlorosoman
| Names | |
|---|---|
| Preferred IUPAC name
3,3-Dimethylbutan-2-yl methylphosphonochloridate | |
| Other names
Pinacolyl methylphosphonochloridate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
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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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Chlorosoman is a chlorine analog of soman. It is a highly toxic organophosphorus compound and 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 degrees Celsius and a melting point of -27 degrees Celsius. Chlorosoman is at least 2.5x less toxic than its analogue.[3]
The 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
[edit | edit source]ClGD 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.
References
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- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Ledgard, J. A Laboratory History of Chemical Warfare Agents.
- ^ cit-OPDC. The preparatory manual to chemical warfare. Vol 1:ClG-agents.
