Chemistry:3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate
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| Names | |
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| Preferred IUPAC name
Pyridin-3-yl 3,3,5-trimethylcyclohexyl methylphosphonate | |
| Other names
EA-1511[1]
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C15H24NO3P | |
| Molar mass | 297.335 g·mol−1 |
| Hazards | |
| Main hazards | Extremely toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
VP (3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate), also known as EA-1511, is an extremely toxic organophosphate nerve agent of the V-series.[2][3]
Agent VP belongs to a class of organophosphates known as 3-pyridyl phosphonates. These agents are extremely potent acetylcholinesterase inhibitors.[4][5]
Synthesis
Methylphosphonic dichloride and triethylamine are dissolved in benzene. 3,3,5-Trimethylcyclohexanol is then slowly added while stirring and cooling. The reaction temperature is maintained at 10 –15 °C. The mixture is then heated to 40 °C for 1 hour. A benzene solution of 3,3,5-trimethylcyclohexyl methylphosphonochloridate is formed.
Triethylamine is then added to reaction mixture and 3-pyridol is added slowly while stirring and cooling. The reaction temperature is maintained at 35 °C. The mixture is then stirred for 1 hour at room temperature. The mixture is washed with a sodium hydroxide solution and water. The solvent is then removed by distillation at reduced pressure to yield the final product. The resulting product can be converted to a quaternary salt by reacting with a haloalkane, such as methyl iodide, to produce a water-soluble agent.[4]
See also
- 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
- A-234 (nerve agent)
- GV (nerve agent)
- Ro 3-0422
- V-sub x
- VT (nerve agent)
References
- ↑ Summary of major events and problems (Report). U.S. Army Chemical Corps. October 1957. https://fas.org/irp/threat/cbw/1957_majoreventsandproblems.pdf.
- ↑ John B. Samuel; Elwin C. Penski; John J. Callahan. Chemical Branch Research Division. ARCSL-SP-83015 - PHYSICAL PROPERTIES OF STANDARD AGENTS, CANDIDATE AGENTS. Commander, Chemical Systems Laboratory; ATTN: DRDAR-CLB-CP - Aberdeen Proving Ground, Maryland 21010. June 1983 [1]
- ↑ Pampalakis, G; Kostoudi, S (11 May 2023). "Chemical, Physical, and Toxicological Properties of V-Agents.". International Journal of Molecular Sciences 24 (10): 8600. doi:10.3390/ijms24108600. PMID 37239944.
- ↑ 4.0 4.1 "3-Pyridyl phosphonates". 1956. https://patents.google.com/patent/US3903098A/en.
- ↑ F. N. Marzulli. Medical Laboratories Special Report No. 75 - A comparison of toxic properties of the V-agents with GB. CMLRE-ML-52. December 1955 [2]
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