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Triphenylmethyl hexafluorophosphate

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Triphenylmethyl hexafluorophosphate
Names
IUPAC name Triphenylcarbenium hexafluorophosphate
Systematic IUPAC name Diphenylmethylbenzene hexafluoridophosphate
Other names
  • Triphenylcarbenium hexafluorophosphate(V)
  • Trityl hexafluorophosphate
  • Tritylium hexafluorophosphate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.467 Edit this at Wikidata
EC Number
  • 207-112-0
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C19H15.F6P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-7(2,3,4,5)6/h1-15H;/q+1;-1Key: IBTFOFOFRZKIJU-UHFFFAOYSA-N
SMILES
  • c1ccc(cc1)(c1ccccc1)c1ccccc1.F(F)(F)(F)(F)F
Properties
Chemical formula [(C6H5)3C][PF6]
Molar mass 388.293 g·mol
Appearance Brown powder
Melting point 145 °C (293 °F; 418 K)
Hazards
GHS labelling:
Pictograms GHS05: Corrosive
Signal word Danger
Hazard statements H314
Precautionary statements P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Triphenylmethyl hexafluorophosphate (also triphenylcarbenium hexafluorophosphate, trityl hexafluorophosphate, or tritylium hexafluorophosphate) is an organic salt with the formula [(C6H5)3C][PF6], consisting of the triphenylcarbenium cation [(C6H5)3C] and the hexafluorophosphate anion [PF6].

Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.

Preparation

Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:

Ag[PF6] + (C6H5)3CCl → [(C6H5)3C][PF6] + AgCl

A second method involves protonolysis of triphenylmethanol:

H[PF6] + (C6H5)3COH → [(C6H5)3C][PF6] + H2O

Structure and reactions

Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses:

[(C6H5)3C][PF6] + H2O → (C6H5)3COH + H[PF6]

Triphenylmethyl hexafluorophosphate has been used for abstracting hydride (H
) from organic compounds. Treatment of metal-alkene and diene complexes one can generate allyl and pentadienyl complexes, respectively.

Triphenylmethyl perchlorate is a common substitute for triphenylmethyl hexafluorophosphate. However, the perchlorate is not used as widely, because, like other organic perchlorates, it is potentially explosive.

See also

References

  1. Triphenylcarbenium hexafluorophosphate from PubChem
  2. ^ Urch, C. (2001). "Triphenylmethyl Hexafluorophosphate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt363f. ISBN 0471936235.
  3. Sharp, D. W. A.; Sheppard, N. (1957). "Complex Fluorides. Part VIII". Journal of the Chemical Society (Resumed): 674–682. doi:10.1039/JR9570000674.
  4. Olah, G.; Svoboda, J.; Olah, J. (1972). "Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts". Synthesis. 1972 (10): 544. doi:10.1055/s-1972-21914.
  5. Fernandez-Galan, R.; Manzano, B; Otero, A; Lanfranchi, M; Pellinghelli, M. (1994). "F and P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution". Inorg. Chem. 33 (10): 2309–2312. doi:10.1021/ic00088a039.
Hexafluorophosphates
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