Tetrakis(triphenylphosphine)palladium Property

Melting point:

103-107 °C

vapor pressure 

0Pa at 25℃

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Fine Powder or Platelets

color 

Bright yellow to khaki

Water Solubility 

insoluble

Sensitive 

Light Sensitive/Air Sensitive

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

BRN 

6704828

Stability:

Light Sensitive, Moisture Sensitive

InChIKey

NANALCPCPBPJAB-UHFFFAOYSA-N

LogP

5.69 at 20℃

CAS DataBase Reference

14221-01-3(CAS DataBase Reference)

EPA Substance Registry System

Palladium, tetrakis(triphenylphosphine)-, (T-4)- (14221-01-3)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

20/22-40-36/37/38

Safety Statements 

22-24/25-36/37-37/39-26

WGK Germany 

3

F 

8-10-23

Hazard Note 

Air sensitive/Light sensitive/Irritant

TSCA 

No

HazardClass 

MOISTURE SENSITIVE, STORED UNDER ARGON

HS Code 

28439090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

Tetrakis(triphenylphosphine)palladium Chemical Properties,Usage,Production

Chemical Properties

yellow crystals

Uses

suzuki reaction

Uses

Pd(PPh3)4 is widely used as a catalyst for palladium-catalyzed coupling reactions. Prominent applications include the Heck reaction, Suzuki coupling, Stille coupling, Sonogashira coupling, and Negishi coupling.

Uses

A high-yielding catalyst used in coupling reactions.

Uses

Tetrakis(triphenylphosphine)palladium(0) is widely used as a catalyst for palladium-catalyzed coupling reactions.

Application

Palladium-Catalyzed Three-Component Reaction for the Synthesis of Imidazolidinones.

Once the Schlenk tube containing K2CO3 (55 mg, 0.40 mmol) is flamed, dried, and filled with argon, Tetrakis(triphenylphosphine)palladium (12 mg, 0.010 mmol), PMB-protected 2,3-allenylamine (37 mg, 0.20 mmol), iodobenzene (58 mg, 0.28 mmol), phenyl isocyanate (36 mg, 0.30 mmol), and CH3CN (4 mL) are added sequentially. The resulting solution is heated to and stirred at 70°C. When the reaction is completed as monitored by TLC, the solvent is evaporated under reduced pressure, and the residue is purified by chromatography on silica gel (petroleum ether : ethyl acetate = 7:1) to afford the corresponding imidazolidione (72 mg, Y. 96%) as an oil.

Reactions

1. Catalyst for Suzuki coupling of chiral secondary organoboronic esters.
2. Palladium-catalyzed SNAr reactions for the synthesis of heteroaryl ethers.
3. Catalyst for cross-coupling of a-diazocarbonyl compouns with arylboronic acids.
4. Diastereoselective synthesis of trans-1,2-diazetidines.
5. Palladium-catalyzed alkynyl iminium ion cyclization.
6. Widely used reagent in a variety of transformations including Heck arylation, enyne and diyne cycloisomerization.
7. Catalysts for cross-coupling.
   
   

Flammability and Explosibility

Non flammable

Purification Methods

The palladium complex is recrystallised from EtOH. It should not be heated excessively as it dissociates to Pd(PPh3)3 and PdPh3 and then further to Pd(PPh3)2 and PPh3. It is also air sensitive as PPh3 is oxidized to PPh3O. It is stable only for short periods because on exposure to heat or air it turns from yellow to orange and dissociates in solution so the solutions should be used directly. However it can always be prepared freshly by mixing Pd(NO3)2 (2mmols) and PPh3(2mmols) in hot *C6H6 when vigorous evolution of nitric oxide occurs and a solid mass separates. This is collected and crystallised from EtOH. Its cryoscopic constant in *C6H6 (at 0.601g/20mL) corresponds to M 1156 [Malatesta & Angoletti J Chem Soc 1186 1957]. It is a useful catalyst for Suzuki coupling reactions [Trost Tetrahedron 33 2615 1977]. [Beilstein 16 IV 954.] This palladium catalyst bound to a polymer support (~0.06mmol/g) is also commercially available [cf Fenger & LeDrain Tetrahedron Lett 39 4287 1998]. [Beilstein 16 IV 954.]