Tetraphenylphosphonium chloride

Tetraphenylphosphonium chloride is the chemical compound with the formula (C₆H₅)₄PCl, abbreviated Ph₄PCl or PPh₄Cl. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in organic solvents.

Structure and basic properties

The cation is tetrahedral. PPh₄Cl crystallises as the anhydrous salt,^[1] which is normal item of commerce, as well as a monohydrate^[2] and a dihydrate.^[3]

In melting point relative to alkyl-based quaternary ammonium salts. Also, since these salts are soluble in organic media, a wide range of solvents can be employed for their crystallisation.

Preparation

The compound was first reported in 1928, when it was prepared via the corresponding bromide salt (CAS# 2751-90-8), which in turn was synthesized by passing dry oxygen through the reaction of triphenylphosphine oxide.

PhMgBr + Ph₃PO → Ph₄POMgBr

Ph₄POMgBr + HBr → Ph₄PBr + “Mg(OH)Br”

PPh₄Cl can also be prepared by the high temperature (>190 °C) reaction of acetylacetonate and by aluminium trichloride.

References

1. ^ J. F. Richardson, J. M. Ball, P. M. Boorman “Structure of Tetraphenylphosphonium Chloride” Acta Crystallographica 1986, volume C42, pp. 1271-1272. doi:10.1107/S0108270186092612.
2. ^ E. E. Schweizer, C. J. Baldacchini, A. L. Rheingold “Tetraphenylphosphonium Chloride Monohydrate, Tetraphenylphosphonium Bromide and Tetraphenylphosphonium Iodide” Acta Crystallographica 1989. volume C45, page 1236-1239. doi:10.1107/S0108270189000363.
3. ^ A. J. Blake, C. D. Garner, J. M. Tunney “Tetraphenylphosphonium Chloride Dihydrate ” Acta Crystallographica 2003, volume E59, o9-o10. doi:10.1107/S1600536802021682
4. ^ Dodonow, J.; Medox, H. “Zur Kenntnis der Grignardschen Reaktion: Über die Darstellung von Tetraphenyl-phosphoniumsalzen” Berichte der deutschen chemischen Gesellschaft 1928, volume 61, pp. 907-911. doi:10.1002/cber.19280610505 10.1002/cber.19280610505.

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