Tetrakis(triphenylphosphine)palladium

Base Information

• Chemical Name: Tetrakis(triphenylphosphine)palladium
• CAS No.: 14221-01-3
• Deprecated CAS: 12582-12-6,136296-64-5,136296-64-5
• Molecular Formula: C72H60P4Pd
• Molecular Weight: 1155.58
• Hs Code.: 28439090
• European Community (EC) Number: 238-086-9
• DSSTox Substance ID: DTXSID9065732
• Nikkaji Number: J3.371.367C
• Wikipedia: Tetrakis(triphenylphosphine)palladium(0)
• Wikidata: Q2366402
• Mol file: 14221-01-3.mol

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Chemical Property of Tetrakis(triphenylphosphine)palladium

Chemical Property:

• Appearance/Colour: yellow crystals
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 103-107 ºC
• Boiling Point: 360oC at 760 mmHg
• Flash Point: 181.7oC
• PSA: 54.36000
• LogP: 13.77920
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive/Air Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 12
• Exact Mass: 1154.26803
• Heavy Atom Count: 77
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Tetrakis(triphenylphosphine)palladium(0) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 20/22-40-36/37/38
• Safety Statements: 22-24/25-36/37-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Organic Compounds, Metal Salts
• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
• Uses: suzuki reaction Tetrakis(triphenylphosphine)palladium(0) is widely used as a catalyst for palladium-catalyzed coupling reactions. 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. A high-yielding catalyst used in coupling reactions.

Technology Process of Tetrakis(triphenylphosphine)palladium

There total 127 articles about Tetrakis(triphenylphosphine)palladium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

palladium tetraammine di(hydrogen carbonate) + triphenylphosphine (603-35-0) → tetrakis(triphenylphosphine) palladium(0) (14221-01-3)

Guidance literature:

In methanol; for 1.5h; Heating / reflux;

Reference yield: 97.6%

triphenylphosphine (603-35-0) + palladium dichloride → tetrakis(triphenylphosphine) palladium(0) (14221-01-3)

Guidance literature:

With sodium hydrogencarbonate; ascorbic acid; In dimethyl sulfoxide; at 20 - 60 ℃; for 2.33333h; Reagent/catalyst;

Reference yield: 95.0%

palladium dichloride → tetrakis(triphenylphosphine) palladium(0) (14221-01-3)

Guidance literature:

With triphenylphosphine; hydrazine; In water; N,N-dimethyl-formamide; N2; refluxing PdCl2 and PPh3 (30 min), addn. of aq. N2H4 (80°C); pptn., filtration, washing (MeOH, ether), drying;

DOI:10.1016/0022-328X(85)87317-4

upstream raw materials:

palladium diacetate

triphenylphosphine

palladium diacetate

tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex

Downstream raw materials:

5'-(3-cyano-4-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

2-(4-methoxyphenyl)-4-methylpyridine

3-(3-cyanopyridin-2-yl)nitrobenzene

4-methoxy-2-(3-nitrophenyl)pyridine

Refernces

• 1、 Min'kov, A. I.,Efimov, O. A.,Eremenko, N. K.. "REDUCTION OF NITROBENZENE IN THE LIQUID PHASE BY CARBON MONOXIDE (II) IN THE PRESENCE OF PALLADIUM COMPLEXES". . p. 899 - 903. Retrieved 1989.
• 2、 Malpass,Hemmings,Wallis,Fletcher,Patel. "Synthesis and nicotinic acetylcholine-binding properties of epibatidine homologues: Homoepibatidine and dihomoepibatidine". . p. 1044 - 1050. Retrieved 2001.
• 3、 Amatore, Christian,Jutand, Anny,M'Barki, Mohamed Amine. "Evidence of the formation of zerovalent palladium from Pd(OAc)2 and triphenylphosphine". . p. 3009 - 3013. Retrieved 1992.
• 4、 Zudin, V. N.,Chinakov, V. D.,Nekipelov, V. M.,Rogov, V. A.,Likholobov, V. A.,Yermakov, Yu. I.. "". . p. 27 - 48. Retrieved 1989.
• 5、 Cui, Peng,Wu, Changjiang,Du, Jun,Luo, Gen,Huang, Zeming,Zhou, Shuangliu. "Three-Coordinate Pd(0) with Rare-Earth Metalloligands: Synergetic CO Activation and Double P-C Bond Cleavage-Formation Reactions". . p. 9688 - 9699. Retrieved 2021.
• 6、 Ioele, Marcella,Ortaggi, Giancarlo,Scarsella, Marco,Sleiter, Giancarlo. "". . p. 2475 - 2476. Retrieved 1991.
• 7、 Salzer, Albrecht,Egolf, Thomas,Philipsborn, Wolfgang von. "Dimetallic Complexes with Bridging Seven-membered Cycloolefins. Synthesis, Multinuclear NMR.-Spectroscopic Properties and Structure". . p. 1145 - 1157. Retrieved 1982.
• 8、 Khalily, Melek Parlak,Gerek?i, Selin,Güle?, Ezgi A.,?zen, Can,?z?ubuk?u, Salih. "Structure-based design, synthesis and anticancer effect of cyclic Smac–polyarginine peptides". . p. 1607 - 1616. Retrieved 2018.
• 9、 Gado, Francesca,Arena, Chiara,Fauci, Cristiana La,Reynoso-Moreno, Ines,Bertini, Simone,Digiacomo, Maria,Meini, Serena,Poli, Giulio,Macchia, Marco,Tuccinardi, Tiziano,Gertsch, Jürg,Chicca, Andrea,Manera, Clementina. "Modification on the 1,2-dihydro-2-oxo-pyridine-3-carboxamide core to obtain multi-target modulators of endocannabinoid system". . . Retrieved 2019/11/11.