Phosphoryl dichloride fluoride

Last updated
Phosphoryl dichloride fluoride
Phosphoryl dichloride fluoride.png
Names
Other names
Phosphorus oxydichlorofluoride, TL-191, Phosphoryl dichlorofluoride
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/Cl2FOP/c1-5(2,3)4
    Key: YNECJZSONMVFHE-UHFFFAOYSA-N
  • O=P(F)(Cl)Cl
Properties
Cl2FOP
Molar mass 136.87 g·mol−1
Boiling point 52 °C [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phosphoryl dichloride fluoride is an inorganic compound with the chemical formula POFCl2.

Contents

Synthesis

It is made by reacting phosphorus pentachloride with potassium monofluorophosphate: [2]

K2PO3F + 2PCl5 → POFCl2 + 2POCl3 + 2KCl

Reactions

The reaction with two equivalents of cyclohexanol yields the nerve agent dicyclohexyl phosphorofluoridate. [3] [4]

The same reaction with isopropanol instead of cyclohexanol yields the nerve agent diisopropyl fluorophosphate. [5]

Two equivalents of sodium azide can replace the chlorine atoms with azide groups. Silver cyanate can replace them with cyanate groups. [6] Hexamethyldisiloxane can replace one of the two chlorine atoms with a trimethylsilyl ether. [7]

References

  1. ↑ Stöckli, Markus J.; Rüedi, Peter (2007). "Synthesis of Enantiomerically Pure 1,5,5-Trideuterated cis- and trans -2,4-Dioxa-3-phosphadecalins. 31 P-NMR Evidence of Covalent-Bond Formation and the Stereochemical Implications in the Course of the Inhibition of δ -Chymotrypsin" . Helvetica Chimica Acta. 90 (11): 2058–2086. doi:10.1002/hlca.200790215. ISSN   0018-019X . Retrieved June 3, 2025.
  2. ↑ Rovnaník, Pavel; Žák, Zdirad; Černík, Miloš (2006-05-29). "Syntheses of Phosphoryl Chloro- and Bromofluorides and Crystal Structures of POFCl 2 and POF 2 Cl" . Zeitschrift für anorganische und allgemeine Chemie. 632 (7): 1356–1362. doi:10.1002/zaac.200500510. ISSN   0044-2313 . Retrieved 2025-06-03.
  3. ↑ Chemical Warfare Agents, and Related Chemical Problems. Parts I-II. 1958.
  4. ↑ Some Aspects Of The Chemistry And Toxic Action Of Organic Compounds Containing Phosphorus And Fluorine. 1957.
  5. ↑ Fest, Christa; Schmidt, Karl-Julius (1982). The Chemistry of Organophosphorus Pesticides. Berlin, Heidelberg: Springer Berlin Heidelberg. p. 82. doi:10.1007/978-3-642-68441-8. ISBN   978-3-642-68443-2 . Retrieved June 3, 2025.
  6. ↑ Song, Chao; Chu, Xianxu; Zhu, Bifeng; Gerken, Michael; Zeng, Xiaoqing (2021). "Synthesis and characterizations of fluorophosphoryl diazide and diisocyanate". Journal of Fluorine Chemistry. 242. Elsevier BV: 109694. Bibcode:2021JFluC.24209694S. doi:10.1016/j.jfluchem.2020.109694. ISSN   0022-1139.
  7. ↑ Rovnanı́k, Pavel; Černı́k, Miloš (2004). "Synthesis and characterisation of trimethylsilyl phosphorohalidates: Me3SiOP(O)FX (X = Cl, Br) and (Me3SiO)2P2O3F2". Journal of Fluorine Chemistry. 125 (1). Elsevier BV: 83–90. doi:10.1016/j.jfluchem.2003.10.006. ISSN   0022-1139.
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