Diisopropyl fluorophosphate – general description and preparation
General description of Diisopropyl fluorophosphate:
Diisopropyl fluorophosphate (DFP, DIFP, DIPF) [55-91-4] or isofluorophate or diisopropyl phosphorofluoridate or phosphoric acid diisopropyl ester fluoride is clear colorless or slightly yellow oily liquid with boiling point of 183 °C.[1] It is a a synthetic dialkyl phosphate with a weak fruity odor. Significant variability has been observed in toxicological studies using commercially available DFP (LD50 values range from 0.0027 mg/kg to 6.4 mg/kg in the mouse model.[2] It is highly toxic by skin absorption and inhalation.
Diisopropyl fluorophosphate is usually made by reaction of isopropyl alcohol with phosphorus trichloride, forming diisopropylphosphite, which is chlorinated and further reacted with sodium fluoride to replace the chlorine atom with fluorine, thus giving diisopropyl fluorophosphate.
Application of Diisopropyl fluorophosphate:
Isofluorophate is a powerful neurotoxin often used in research studies as a surrogate for organophosphorus nerve agents such as sarin (GB) and soman (GD) due to its ability to effectively inhibit the enzyme acetylcholinesterase.[3] It is typical example of organophosphorus insecticide, firstly patented by Monsanto chemical company in 1944.[4] DFP is known to bind and inhibit serine proteases and other unidentified esterases. DFP has been used and is still used as a tool for many toxicological and pharmacological applications in which the consequence of protease inhibition or cholinergic effects is needed to study a pharmacological or cell biology process.[5]
[1] B. C. Saunders, G. J. Stacey J. Chem. Soc.1984, 695. Doi: 10.1039/JR9480000695. [2] K.L. Brewer, M. M. Troendle, L. Pekman, W. J. Meggs Am. J. Emerg. Med. 2013, 31, 676. Doi: 10.1016/j.ajem.2012.12.003. [3] D. R. Heiss, D. W. Zehnder II, D. A. Jett, G. E. Platoff Jr., D. T. Yeung, B. N. Brewer J. Chem. 2016 Doi: 10.1155/2016/3190891. [4] E. E. Hardy, G. M. Kosolapoff Halogenated compounds and process for making same 1944, Monsanto Chemicals Ltd. US2409039A. [5] Miguel Sogorb, Jorge Estevez, Eugenio Vilanova, Chapter 57 – Toxicokinetics and Toxicodynamics of DFP 2015 Doi: 10.1016/B978-0-12-800159-2.00057-9.
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January 26, 2023