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Tetrakis(triphenylphosphine)palladium

CAS No.
14221-01-3
Chemical Name:
Tetrakis(triphenylphosphine)palladium
Synonyms
PD(PPH3)4;TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0);etrakis(triphenylphosphine)palladiuM;TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(O);PALLADIUM (0) TETRAKIS(TRIPHENYLPHOSPHINE);Tetra(triphenylphosphine) palladium;Tetrakis(triphenylphosphine)palladiu;PALLADIUM-TETRAKIS(TRIPHENYLPHOSPHINE);Tetrakis(triphenylphosphine)palladium, tech;Tetrakis(triphenylphosphine)palladium(0), 99.8% (metals basis), Pd 9% min
CBNumber:
CB6163934
Molecular Formula:
C72H60P4Pd
Molecular Weight:
1155.561844
MDL Number:
MFCD00010012
MOL File:
14221-01-3.mol
MSDS File:
SDS
Last updated:2024-04-22 19:50:33

Tetrakis(triphenylphosphine)palladium Properties

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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
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
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

Tetrakis(triphenylphosphine)palladium price More Price(60)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 500mg $109 2024-03-01 Buy
Sigma-Aldrich 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 1g $162 2024-03-01 Buy
Sigma-Aldrich 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 5G $456 2024-03-01 Buy
Sigma-Aldrich 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 25g $1180 2024-03-01 Buy
Sigma-Aldrich 216666 Tetrakis(triphenylphosphine)palladium(0) 99% 14221-01-3 1g $44.5 2024-03-01 Buy
Product number Packaging Price Buy
8.14761 500mg $109 Buy
8.14761 1g $162 Buy
8.14761 5G $456 Buy
8.14761 25g $1180 Buy
216666 1g $44.5 Buy

Tetrakis(triphenylphosphine)palladium Chemical Properties,Uses,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.
Palladium-Catalyzed Three-Component Reaction for the Synthesis of Imidazolidinones.gif
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.
    Tetrakis(triphenylphosphine)palladium Reaction 1
    Tetrakis(triphenylphosphine)palladium Reaction 2

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.]

13965-03-2
14221-01-3
Synthesis of Tetrakis(triphenylphosphine)palladium from Bis(triphenylphosphine)palladium(II) chloride
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View Lastest Price from Tetrakis(triphenylphosphine)palladium manufacturers

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Tetrakis(triphenylphosphine)palladium pictures 2024-04-22 Tetrakis(triphenylphosphine)palladium
14221-01-3
US $10.00 / kg 1kg 99.8% 10000ton Ouhuang Engineering Materials (Hubei) Co., Ltd
Tetrakis(triphenylphosphine)palladium pictures 2024-03-15 Tetrakis(triphenylphosphine)palladium
14221-01-3
US $8.70-6.50 / kg 500kg 99.9 200tons Shandong Juchuang Chemical Co., LTD
Tetrakis(triphenylphosphine)palladium(0) pictures 2024-02-23 Tetrakis(triphenylphosphine)palladium(0)
14221-01-3
US $111.00-422.00 / g 5g 0.98 25kg Shanghai UCHEM Inc.
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