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Tetraphenylphosphonium chloride

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Tetraphenylphosphonium chloride Basic information

Product Name:
Tetraphenylphosphonium chloride
Synonyms:
  • TETRAPHENYLPHOSPHONIUM CHLORIDE
  • TETRAPHENYLPHOSPHONIUM CHLORID
  • Phosphonium, tetraphenyl-, chloride
  • Tetraphenylchlorophosphine
  • TETRAPHENYLPHOSPONIUM CHLORIDE
  • Tetraphenylphosphonium chloride, C 73.8%, H 5.5%
  • Tetraphenylphosphanium chloride
  • Tetraphenylphosphonium chloride,98%
CAS:
2001-45-8
MF:
C24H20ClP
MW:
374.84
EINECS:
217-890-3
Product Categories:
  • Liqiud crystal intermediates
  • Greener Alternatives: Catalysis
  • Phosphonium Compounds
  • Phase Transfer Catalysts
  • Phosphonium Salts
Mol File:
2001-45-8.mol
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Tetraphenylphosphonium chloride Chemical Properties

Melting point:
272-274 °C(lit.)
storage temp. 
Inert atmosphere,Room Temperature
form 
Crystalline Powder
color 
White to beige
Water Solubility 
Soluble in water.
Sensitive 
Hygroscopic
BRN 
3922393
CAS DataBase Reference
2001-45-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
3-10
HS Code 
29310095

MSDS

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Tetraphenylphosphonium chloride Usage And Synthesis

Chemical Properties

White to beige crystalline powder

Uses

Tetraphenylphosphonium chloride 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.

Preparation

Tetraphenylphosphonium chloride(PPh4Cl) and many analogous compounds can be prepared by the reaction of chlorobenzene with triphenylphosphine catalysed by nickel salts:
PhCl + PPh3 → Ph4PCl

Application

Tetraphenylphosphonium chloride can be used to tune the crystallinity of CH3NH3PbI3 thin film during the deposition for boosting perovskite solar cells (PSCs) device performance. It can also be used as arylating reagents in Pd-catalyzed Heck reaction.

Reactions

Tetraphenylphosphonium chloride reacts with organometallic anionic complexes to give the corresponding salts. Depending on the size of the alkyl groups, the reaction of tetraphenylphosphonium chloride with a lithium dialkylamide can proceed in two directions to give 9-phenyl-9-phosphafluorene and benzene, or triphenylphosphine and the dialkylaniline. Lithium monoalkylamides react with tetraphenylphosphonium chloride to give (also depending on the size of the substituents) either N-alkyltriphenylphosphines or phosphine.

Purification Methods

Crystallise the chloride from acetone and dry at 70o under vacuum. It can also be recrystallised from a mixture of 1:1 or 1:2 dichloromethane/pet ether, the solvents having been dried over anhydrous K2CO3. The purified salt is dried at room temperature under a vacuum for 3days, and at 170o for a further 3days. Also recrystallise it from isoPrOH/Et2O or EtOH/Et2O. Extremely hygroscopic. [Wittig & Geissler Justus Liebigs Ann Chem 580 44, 50 1953, Willard et al. J Am Chem Soc 70 737 1948, Beilstein 16 III 851, 16 IV 984.]

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