Chlorosoman

Names
	Preferred IUPAC name 3,3-Dimethylbutan-2-yl methylphosphonochloridate
	Other names Pinacolyl methylphosphonochloridate
Identifiers
CAS Number	7040-57-5;
3D model (JSmol)	Interactive image;
ChemSpider	128777;
PubChem CID	145983;
CompTox Dashboard (EPA)	DTXSID80863993 ;
	InChI InChI=1S/C7H16ClO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3 Key: XVNBZVNXJMOQEX-UHFFFAOYSA-N;
	SMILES CC(C(C)(C)C)OP(=O)(C)Cl;
Properties
Chemical formula	C7H16ClO2P
Molar mass	198.63 g·mol−1
Solubility in water	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

Chlorosoman

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]

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↓

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.

[PubChem-1] 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] t-OPDC. The preparatory manual to chemical warfare. Vol 1:ClG-agents.