Triphenylmethyl hexafluorophosphate

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]⁻.^[1]

Triphenylmethyl hexafluorophosphate

Names
IUPAC name Triphenylcarbenium hexafluorophosphate
Systematic IUPAC name Diphenylmethylbenzene hexafluoridophosphate
Other names Triphenylcarbenium hexafluorophosphate(V) Trityl hexafluorophosphate Tritylium hexafluorophosphate
Identifiers
CAS Number	437-17-2 Y
3D model (JSmol)	Interactive image
ChemSpider	2006130
ECHA InfoCard	100.006.467
EC Number	207-112-0
PubChem CID	2723954
CompTox Dashboard (EPA)	DTXSID40883238
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;-1 Key: IBTFOFOFRZKIJU-UHFFFAOYSA-N
SMILES c1ccc(cc1)[C+](c1ccccc1)c1ccccc1.F[P-](F)(F)(F)(F)F
Properties
Chemical formula	[(C6H5)3C]+[PF6]−
Molar mass	388.293 g·mol−1
Appearance	Brown powder
Melting point	145 °C (293 °F; 418 K)
Hazards
GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.^[2]

Preparation

Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:^[3]

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

A second method involves protonolysis of triphenylmethanol:^[4]

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:^[5]

[(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.^[2]

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.^[2]

See also

• Triphenylmethyl radical
• Triphenylcarbenium
• Triphenylmethane
• Triphenylmethanol
• Triphenylmethyl chloride