Triphenylmethyl hexafluorophosphate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Triphenylmethyl hexafluorophosphate
Ph3CPF6.png
Names
Other names
Trityl hexafluorophosphate
Triphenylcarbenium hexafluorophosphate
Identifiers
ECHA InfoCard 100.006.467
Properties
C19H15F6P
Molar mass 388.31 g/mol
Appearance brown powder
Melting point 145 °C (293 °F; 418 K)
Hazards
Safety data sheet [1]
R-phrases (outdated) R34, R26, R36/37, R39, R45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Triphenylmethyl hexafluorophosphate is an organic salt with the formula (C6H5)3CPF6. It is a brown powder that hydrolyzes readily to triphenylmethanol. Triphenylmethyl hexafluorophosphate is used as a catalyst and reagent in organic syntheses.[1]

Preparation[edit]

Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:[2]

AgPF6 + (C6H5)3CCl → (C6H5)3CPF6 + AgCl

A second method involves protonolysis of generating triphenylmethanol :[3]

HPF6 + (C6H5)3COH → (C6H5)3CPF6 + H2O

Structure and reactions[edit]

Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses:[4]

(C6H5)3CPF6 + H2O → (C6H5)3COH + HPF6

Triphenylmethyl hexafluorophosphate has been used for abstracting hydride. Treatment of metal-alkene and diene complexes one can generate allyl and pentadienyl complexes, respectively.[1]

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.[1]

Triarylmethane dyes[edit]

Triarylmethane dyes are derivatives are stabilized version of the trityl cation, so much so that they are water-soluble and are often obtained as the chloride salts. These dyes have strong electron donor groups, often amines, at the p-positions of two or three of the aryl groups.[5]

See also[edit]

References[edit]

  1. ^ a b c Urch, C. (2001). "Triphenylmethyl Hexafluorophosphate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt363f. ISBN 0471936235. 
  2. ^ Sharp, D., Shepard, N. (1956). "Complex Fluorides. Part VIII". University Chemical Laboratory, Cambridge: 674–682. 
  3. ^ 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. 
  4. ^ Fernandez-Galan, R.; Manzano, B; Otero, A; Lanfranchi, M; Pellinghelli, M. (1994). "19F and 31P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution". Inorg. Chem. 33 (10): 2309–2312. doi:10.1021/ic00088a039. 
  5. ^ Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a27_179