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HomeProduct name listTetraphenylphosphonium chloride

Tetraphenylphosphonium chloride

  • CAS NO.:2001-45-8
  • Empirical Formula: C24H20ClP
  • Molecular Weight: 374.84
  • MDL number: MFCD00011916
  • EINECS: 217-890-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-12 17:17:06
Tetraphenylphosphonium chloride Structural

What is Tetraphenylphosphonium chloride?

Chemical properties

White to beige crystalline powder

The Uses of Tetraphenylphosphonium chloride

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

What are the applications of 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.]

Properties of Tetraphenylphosphonium chloride

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)

Safety information for Tetraphenylphosphonium chloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Tetraphenylphosphonium chloride

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