Chlorosoman
{{Chembox
| Name = Chlorosoman
| ImageFile =Chlorosoman.png
| ImageFile1 =Chlorosoman-3D.png
| PIN = 3,3-Dimethylbutan-2-yl methylphosphonochloridate
| OtherNames = Pinacolyl methylphosphonochloridate
| Section1 = {{Chembox Identifiers
| CASNo = 7040-57-5
| PubChem = 145983
| ChemSpiderID = 128777
| SMILES = CC(C(C)(C)C)OP(=O)(C)Cl
| InChI = InChI=1S/C7H16ClO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3
| InChIKey = XVNBZVNXJMOQEX-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=7 | H=16| Cl=1 | O=2 | P=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = 1,030 mg/L{{cite web
| url=https://pubchem.ncbi.nlm.nih.gov/compound/145983
| title=Chlorosoman - PubChem Compound Database
| access-date=2018-05-26
| author=National Center for Biotechnology Information
| archive-date=2019-04-28
| archive-url=https://web.archive.org/web/20190428162323/https://pubchem.ncbi.nlm.nih.gov/compound/145983
| url-status=live
}}
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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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.{{Cite journal | doi = 10.1002/slct.201702763| title = Precursors of Nerve Chemical Warfare Agents with Industrial Relevance: Characteristics and Significance for Chemical Security| journal = ChemistrySelect| volume = 3| issue = 10| pages = 2703–2715| year = 2018| last1 = Quagliano| first1 = Javier| last2 = Witkiewicz| first2 = Zygfryd| last3 = Sliwka| first3 = Ewa| last4 = Neffe| first4 = Slawomir}} 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.Ledgard, J. A Laboratory History of Chemical Warfare Agents.
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.cit-OPDC. The preparatory manual to chemical warfare. Vol 1:ClG-agents. 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.