Chlorosoman
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| Names | |
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| 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 | |
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).
Infobox references
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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
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.
![{\displaystyle {6\,\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}\mathrm {P} (\mathrm {O} )\mathrm {FOCH} {\vphantom {A}}_{\smash[{t}]{3}}\mathrm {CHC} (\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{3}}{}+{}\mathrm {AlCl} {\vphantom {A}}_{\smash[{t}]{3}}{}+{}3\,\mathrm {NaCl} {}\mathrel {\longrightarrow } {}6\,\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}\mathrm {P} (\mathrm {O} )\mathrm {ClOCH} {\vphantom {A}}_{\smash[{t}]{3}}\mathrm {CHC} (\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{3}}{}+{}\mathrm {Na} {\vphantom {A}}_{\smash[{t}]{3}}\mathrm {AlF} {\vphantom {A}}_{\smash[{t}]{6}}\mathrm {v} }}](./_assets_/77b895b5b90401e1325b5aaa037dec7710c5b124.svg)
References
- ^ a b National Center for Biotechnology Information. "Chlorosoman - PubChem Compound Database". Archived from the original on 2019-04-28. Retrieved 2018-05-26.
- ^ Quagliano, Javier; Witkiewicz, Zygfryd; Sliwka, Ewa; Neffe, Slawomir (2018). "Precursors of Nerve Chemical Warfare Agents with Industrial Relevance: Characteristics and Significance for Chemical Security". ChemistrySelect. 3 (10): 2703–2715. doi:10.1002/slct.201702763.
- ^ Ledgard, J. A Laboratory History of Chemical Warfare Agents.
- ^ cit-OPDC. The preparatory manual to chemical warfare. Vol 1:ClG-agents.