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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Extremely toxic |
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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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]
Agent VP belongs to a class of organophosphates known as 3-pyridyl phosphonates. These agents are extremely potent acetylcholinesterase inhibitors.[3][4]
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.[3]
See also
- 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
- A-234 (nerve agent)
- GV (nerve agent)
- Ro 3-0422
- V-sub x
References
- ^ Summary of major events and problems (PDF) (Report). U.S. Army Chemical Corps. October 1957 – via fas.org.
- ^ 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]
- ^ a b "3-Pyridyl phosphonates". Google Patents. 1956.
- ^ 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]