Tetraphenylphosphonium chloride

Tetraphenylphosphonium chloride

Names
IUPAC name Tetraphenylphosphonium chloride
Identifiers
CAS Registry Number	2001-45-8 N
ChEMBL	ChEMBL223885 Y
ChemSpider	144578 Y
InChI InChI=1S/C24H20P.ClH/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;/h1-20H;1H/q+1;/p-1 Y Key: WAGFXJQAIZNSEQ-UHFFFAOYSA-M Y InChI=1S/C24H20P.ClH/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;/h1-20H;1H/q+1;/p-1 Key: WAGFXJQAIZNSEQ-REWHXWOFAO
Jmol-3D images	Image
PubChem	164911
SMILES [Cl-].c1c(cccc1)[P+](c2ccccc2)(c3ccccc3)c4ccccc4
Properties
Chemical formula	C24H20ClP
Molar mass	374.84 g/mol
Appearance	colourless solid
Density	1.27
Melting point	272 to 274 °C (522 to 525 °F; 545 to 547 K)
Hazards
R-phrases	36/37/38
S-phrases	26-36
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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

Preparation

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"

References