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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Cyclohexyl methylphosphonofluoridate | |||
| Other names GF;(Fluoro-methyl-phosphoryl)oxycyclohexane | |||
| Identifiers | |||
| |||
3D model (JSmol) | |||
| ChemSpider |
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| UNII | |||
| UN number | 2810 | ||
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| Properties | |||
| C7H14FO2P | |||
| Molar mass | 180.159 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 1.1278 g/cm3 | ||
| Melting point | −30 °C (−22 °F; 243 K) | ||
| Boiling point | 239 °C (462 °F; 512 K) | ||
| Almost insoluble | |||
| Hazards | |||
| Flash point | 94 °C (201 °F; 367 K) | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Cyclosarin orGF (cyclohexyl methylphosphonofluoridate) is an extremelytoxic substance used as achemical weapon.[1] It is a member of theG-series family ofnerve agents, a group ofchemical weapons discovered and synthesized by a German team led byGerhard Schrader. The major nerve gases are the G agents,sarin (GB),soman (GD),tabun (GA), and the V agents such asVX. The original agent, tabun, was discovered in Germany in 1936 in the process of work onorganophosphorusinsecticides. Next came sarin, soman and finally, cyclosarin, a product of commercial insecticide laboratories prior toWorld War II.
As achemical weapon, it is classified as aweapon of mass destruction by theUnited Nations. Pursuant toUN Resolution 687 its production and stockpiling was outlawed globally by theChemical Weapons Convention (CWC) of 1993, although Egypt, Israel, North Korea and South Sudan have not ratified the CWC (thus not outlawing their own stockpiling of chemical weapons).
Like its predecessorsarin, cyclosarin is a liquidorganophosphate nerve agent. Its physical characteristics are, however, quite different from those of sarin.
Atroom temperature, cyclosarin is a colorless liquid whose odor has been variously described as sweet and musty,[2] or resemblingpeaches orshellac. Unlike sarin, cyclosarin is apersistent liquid, meaning that it has a lowvapor pressure and thereforeevaporates relatively slowly, at only about 1/69th the rate of sarin and 1/20th that of water.
Also unlike sarin, cyclosarin isflammable, with aflash point of 94 °C (201 °F).
First synthesized duringWorld War II as part ofNazi Germany's chemical weapons research on organophosphate compounds after their military potential was recognized, cyclosarin was also studied later in theUnited States andGreat Britain in the early 1950s as part of a systematic study of potential nerve agents. It was never selected formass production, however, due to itsprecursors being more expensive than those of other G-series nerve agents such as sarin (GB).
To date, Iraq is the only nation known to have manufactured significant quantities of cyclosarin for use as achemical agent and to deploy it in battle. During theIran–Iraq War (1980–1988), the Iraqis used sarin and cyclosarin together as a mixture. This was likely done to obtain a more persistent chemical agent as well as in response to an existing embargo placed on alcohol precursors for sarin.[3]
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Like other nerve agents, cyclosarin can be shipped inbinary munitions.
A cyclosarin binary weapon would most likely containmethylphosphonyl difluoride in one capsule, with the other capsule containing a mixture ofcyclohexylamine andcyclohexanol.
Iraq fielded munitions filled with a mixture of GB (sarin) and GF (cyclosarin). Tests on mice indicated that GB-GF mixtures have a relative toxicity between GF and GB.[4]
