Mipafox

Mipafox

Names
Preferred IUPAC name N,N′-Di(propan-2-yl)phosphorodiamidic fluoride
Other names Bis(isopropylamino)fluorophosphine oxide; Isopestox
Identifiers
CAS Number	371-86-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82142
ChemSpider	9355
ECHA InfoCard	100.006.130
EC Number	206-742-3
KEGG	C19008
PubChem CID	9738
UNII	24MJP5H3YN
CompTox Dashboard (EPA)	DTXSID5042160
InChI InChI=1S/C6H16FN2OP/c1-5(2)8-11(7,10)9-6(3)4/h5-6H,1-4H3,(H2,8,9,10) Key: UOSHUBFBCPGQAY-UHFFFAOYSA-N
SMILES CC(C)NP(=O)(NC(C)C)F
Properties
Chemical formula	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)
Solubility in water	80 g/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H370
Precautionary statements	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). Infobox references

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

There are case reports of delayed neurotoxicity and paralysis due to acute exposure to mipafox. ^[3]

Synthesis

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

• Dimefox
• Schradan

References

1. 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. Bibcode:2016ArTox..90..603M. doi:10.1007/s00204-015-1481-1. PMC   4833118 . PMID   25743373.
2. "The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019" (PDF). World Health Organization.
3. 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.
4. "Process for the preparation of bisisopropyl-amino-fluoro-phosphine oxide".