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Tetrakis(triphenylphosphine)palladium

CAS No.14221-01-3
Chemical Name:Tetrakis(triphenylphosphine)palladium
CBNumber:CB6163934
Molecular Formula:C72H60P4Pd
Formula Weight:1155.561844
MOL File:14221-01-3.mol

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
Hydrolytic Sensitivity 7: reacts slowly with moisture/water
Sensitive Light Sensitive/Air Sensitive
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)
FDA UNII N9O1RWZ93J
EPA Substance Registry System Palladium, tetrakis(triphenylphosphine)-, (T-4)- (14221-01-3)
UNSPSC Code 12352200
NACRES NA.22

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

NFPA 704:

	0
1		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264-P270-P301+P312-P501

Tetrakis(triphenylphosphine)palladium Price More Price(20)

Brand: Sigma-Aldrich(India)
Product number: 8.14761
Product name : Tetrakis(triphenylphosphine)-palladium(0)
Purity: for synthesis
Packaging: 500MG
Price: ₹4880
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 8.14761
Product name : Tetrakis(triphenylphosphine)-palladium(0)
Purity: for synthesis
Packaging: 1G
Price: ₹7230
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 8.14761
Product name : Tetrakis(triphenylphosphine)-palladium(0)
Purity: for synthesis
Packaging: 5G
Price: ₹21680
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 8.14761
Product name : Tetrakis(triphenylphosphine)-palladium(0)
Purity: for synthesis
Packaging: 25G
Price: ₹75120.01
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 216666
Product name : Tetrakis(triphenylphosphine)palladium(0)
Purity: 99%
Packaging: 1G
Price: ₹6250
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Tetrakis(triphenylphosphine)palladium Chemical Properties,Usage,Production

Chemical Properties yellow crystals
Uses A high-yielding catalyst used in coupling reactions.
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 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
reaction suitability reagent type: catalyst
reaction type: Cross Couplings
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.]