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Tetrakis(triphenylphosphine)palladium

Tetrakis(triphenylphosphine)palladium Structure
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
MOL File:
14221-01-3.mol
MSDS File:
SDS
Modify Date:
2024/4/22 19:50:33
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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)
EPA Substance Registry System Palladium, tetrakis(triphenylphosphine)-, (T-4)- (14221-01-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
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
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

Tetrakis(triphenylphosphine)palladium price More Price(20)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 500MG ₹4880 2022-06-14 Buy
Sigma-Aldrich(India) 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 1G ₹7230 2022-06-14 Buy
Sigma-Aldrich(India) 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 5G ₹21680 2022-06-14 Buy
Sigma-Aldrich(India) 8.14761 Tetrakis(triphenylphosphine)-palladium(0) for synthesis 14221-01-3 25G ₹75120.01 2022-06-14 Buy
Sigma-Aldrich(India) 216666 Tetrakis(triphenylphosphine)palladium(0) 99% 14221-01-3 1G ₹6250 2022-06-14 Buy
Product number Packaging Price Buy
8.14761 500MG ₹4880 Buy
8.14761 1G ₹7230 Buy
8.14761 5G ₹21680 Buy
8.14761 25G ₹75120.01 Buy
216666 1G ₹6250 Buy

Tetrakis(triphenylphosphine)palladium Chemical Properties,Uses,Production

Chemical Properties

yellow crystals

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

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.]

Tetrakis(triphenylphosphine)palladium Preparation Products And Raw materials

Raw materials

Hydrazinium hydroxide solution Acetonitrile Ethanol tert-Butyl methyl ether Toluene
Hydrazine hydrate Diethyl ether Palladium chloride Ethyl acetate Dimethyl sulfoxide
Triphenylphosphine
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Preparation Products

3-AMINOBIPHENYL 3-(6-FORMYL-PYRIDIN-2-YL)-BENZONITRILE 6-(3-NITROPHENYL)-2-PYRIDINECARBOXALDEHYDE 6-(4-METHYLSULFANYLPHENYL)PYRIDINE-2-CARBALDEHYDE 6-(4-METHOXYPHENYL)PYRIDINE-2-CARBALDEHYDE
PLUMBAGIN 6-(THIOPHEN-3-YL)PYRIDINE-2-CARBALDEHYDE Dimidium bromide 3-AMINO-6-PHENYLPYRIDAZINE 4-PHENYLETHYNYLPHTHALIC ANHYDRIDE
2-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE 6-(4-FLUOROPHENYL)PYRIDINE-2-CARBALDEHYDE 4-(6-FORMYLPYRIDIN-2-YL)BENZONITRILE 3-(3-PYRIDINYL)BENZOIC ACID 1-(3-AMINO-PYRIDIN-2-YL)-ETHANONE
6-(2-THIENYL)-2-PYRIDINECARBOXALDEHYDE 4-Hex-1-ynylbenzaldehyde 4-BENZYLOXY-3-INDOLEACETONITRILE 6-(4-CHLOROPHENYL)PYRIDINE-2-CARBALDEHYDE 3-(4-METHYLPHENYL)BENZALDEHYDE
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Tetrakis(triphenylphosphine)palladium Suppliers

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DAVY CHEM LABS 58
JIVICHEM SYNTHESIS PVT LTD 58
Evans Fine Chem 58
JSK Chemicals 58
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Vineeth Precious Catalysts Pvt Ltd 58
Omkar Lab 58
ALS INDIA LIFE SCIENCES 58
Metal Chem India 58
Innovassynth Technologies (I) Ltd. 58

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