World Library  
Flag as Inappropriate
Email this Article

Tetraphenylphosphonium chloride

Article Id: WHEBN0010122392
Reproduction Date:

Title: Tetraphenylphosphonium chloride  
Author: World Heritage Encyclopedia
Language: English
Subject: Counterion, Triphenylphosphine dichloride
Publisher: World Heritage Encyclopedia

Tetraphenylphosphonium chloride

Template:Chembox ChEMBL
Tetraphenylphosphonium chloride
CAS number 2001-45-8 N
PubChem 164911
ChemSpider 144578 YesY
Jmol-3D images Image 1
Molecular formula C24H20ClP
Molar mass 374.84 g/mol
Appearance colourless solid
Density 1.27
Melting point

272–274 °C

R-phrases 36/37/38
S-phrases 26-36
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 gravimetric analysis of perchlorate and related oxyanions. This colourless salt is used to generate lipophilic salts from inorganic and organometallic anions. Thus, Ph4P+ is useful as a phase-transfer catalyst, again because it allows inorganic anions to dissolve 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 X-ray crystallography, PPh4+ salts are of interest as they often crystallise easily. The rigidity of the phenyl groups facilitates packing and elevates the 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.

constituent ions in the solid
space-filling model of part
of the crystal structure
ball-and-stick model of part
of the crystal structure


PPh4Cl and many analogous compounds can be prepared by the reaction of chlorobenzene with triphenylphosphine catalysed by nickel salts:[4]

PhCl + PPh3 → Ph4PCl

The compound was originally prepared as the corresponding bromide salt (CAS# 2751-90-8), which in turn was synthesized by passing dry oxygen through the reaction of phenylmagnesium bromide and triphenylphosphine[5] The synthesis probably proceeds via the reaction of the Grignard reagent with triphenylphosphine oxide.

PhMgBr + Ph3PO → Ph4POMgBr
Ph4POMgBr + HBr → Ph4PBr + "Mg(OH)Br"


This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.