3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate

VP
Names
	Preferred IUPAC name Pyridin-3-yl 3,3,5-trimethylcyclohexyl methylphosphonate
	Other names EA-1511
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	139033580;
CompTox Dashboard (EPA)	DTXSID501020092;
	show InChI
	show SMILES
Properties
Chemical formula	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.

Agent VP belongs to a class of organophosphates known as 3-pyridyl phosphonates. These agents are extremely potent acetylcholinesterase inhibitors.^[2]

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 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.^[2]

References[]

^ Summary of major events and problems (PDF) (Report). U.S. Army Chemical Corps. October 1957 – via fas.org.
^ Jump up to: ^a ^b "3-Pyridyl phosphonates". Google Patents. 1956.

[1] Summary of major events and problems (PDF) (Report). U.S. Army Chemical Corps. October 1957 – via fas.org.

[VP-2] Jump up to: ^a ^b "3-Pyridyl phosphonates". Google Patents. 1956.

[1]

[2]

show v t Neurotoxins
	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Guanitoxin BMAA Saxitoxin
Plant toxins	Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN

Names

Preferred IUPAC name Pyridin-3-yl 3,3,5-trimethylcyclohexyl methylphosphonate
Other names EA-1511^[1]
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	139033580
CompTox Dashboard (EPA)	DTXSID501020092
show InChI InChI=1S/C15H24NO3P/c1-12-8-14(10-15(2,3)9-12)19-20(4,17)18-13-6-5-7-16-11-13/h5-7,11-12,14H,8-10H2,1-4H3 Key: KQWAOLPZVUPXQI-UHFFFAOYSA-N
show SMILES CC2CC(OP(C)(=O)Oc1cccnc1)CC(C)(C)C2
Properties
Chemical formula	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

3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate

Synthesis[]

See also[]

References[]