Mipafox
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| Names | |
|---|---|
| Preferred IUPAC name
N,N′-Di(propan-2-yl)phosphorodiamidic fluoride | |
| Other names
Bis(isopropylamino)fluorophosphine oxide; Isopestox
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.130 |
| EC Number |
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| KEGG | |
PubChem CID
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|
| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H16FN2OP | |
| Molar mass | 182.179 g·mol−1 |
| Density | 1.2 |
| Melting point | 65 °C (149 °F; 338 K) |
| Boiling point | 125 °C (257 °F; 398 K) |
| 80 g/L | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Highly toxic |
| GHS labelling: | |
 
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| Danger | |
| H301, H370 | |
| P260, P264, P270, P301+P310, P307+P311, P321, P330, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mipafox is a highly toxic organophosphate insecticide that is an irreversible acetylcholinesterase inhibitor and is resistant to cholinesterase reactivators.[1] It was developed in the 1950s and is now believed to be no longer in use.[2]
Toxicity
[edit]There are case reports of delayed neurotoxicity and paralysis due to acute exposure to mipafox.[3]
Synthesis
[edit]Phosphoryl chloride is first reacted with isopropylamine. The resulting product is then reacted with potassium fluoride or ammonium fluoride to produce mipafox.[4]
See also
[edit]References
[edit]- ^ Mangas, I; Taylor, P; Vilanova, E; Estévez, J; França, TC; Komives, E; Radić, Z (March 2016). "Resolving pathways of interaction of mipafox and a sarin analog with human acetylcholinesterase by kinetics, mass spectrometry and molecular modeling approaches". Archives of Toxicology. 90 (3): 603–16. doi:10.1007/s00204-015-1481-1. PMC 4833118. PMID 25743373.
- ^ "The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019" (PDF). World Health Organization.
- ^ BIDSTRUP, PL; BONNELL, JA; BECKETT, AG (16 May 1953). "Paralysis following poisoning by a new organic phosphorus insecticide (mipafox); report on two cases". British Medical Journal. 1 (4819): 1068–72. doi:10.1136/bmj.1.4819.1068. PMC 2016450. PMID 13042137.
- ^ "Process for the preparation of bisisopropyl-amino-fluoro-phosphine oxide".
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