Chlorosoman
Names
Preferred IUPAC name
3,3-Dimethylbutan-2-yl methylphosphonochloridate
Other names
Pinacolyl methylphosphonochloridate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C7H16ClO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3
    Key: XVNBZVNXJMOQEX-UHFFFAOYSA-N
  • CC(C(C)(C)C)OP(=O)(C)Cl
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).

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]

References

  1. ^ a b National Center for Biotechnology Information. "Chlorosoman - PubChem Compound Database". Archived from the original on 2019-04-28. Retrieved 2018-05-26.
  2. ^ 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.
  3. ^ Ledgard, J. A Laboratory History of Chemical Warfare Agents.
  4. ^ cit-OPDC. The preparatory manual to chemical warfare. Vol 1:ClG-agents.


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