14588-08-0

Basic information

• Product Name: Bis(triphenylphosphinepalladium) acetate
• Synonyms: Diacetatobis(triphenylphosphine)palladium(II) Store refrigerated;Bis(acetato)bis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) diacetate;Palladium, bis(acetato-O)bis(triphenylphosphine)-;Diacetatobis(triphenylphosphine)palladium(II), Pd 14.2%;Bis(triphenylphosphine)palladium(II) acetate,99%;Diacetatobis(Triphenylphosphosphate) PalladiuM;Diacetatobis(triphenylphosphine)palladiuM(II),98% (PPh3)2Pd(OAc)2;Bis(triphenylphosphinepalladiu
• CAS NO: 14588-08-0
• Molecular Formula: C₄₀H₃₆O₄P₂Pd
• Molecular Weight: 749.08
• EINECS: 238-628-4
• Product Categories: Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes;Pd (Palladium) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;metal-phosphine complexes;chemical reaction,pharm,electronic,materials;Halogenated Heterocycles ,Pyrimidines;Pd;Metal Compounds
• Mol File: 14588-08-0.mol

Chemical Properties

• Melting Point: 136 °C (dec.)(lit.)
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 181.7 °C
• Appearance: Yellow/Powder
• Vapor Pressure: 4.74E-05mmHg at 25°C
• Storage Temp.: −20°C
• Stability: store cold
• CAS DataBase Reference: Bis(triphenylphosphinepalladium) acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(triphenylphosphinepalladium) acetate(14588-08-0)
• EPA Substance Registry System: Bis(triphenylphosphinepalladium) acetate(14588-08-0)

Safety Data

• Hazard Codes: Xn
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 1-3-10
• Hazardous Substances Data: 14588-08-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Bis(triphenylphosphinepalladium) acetate is used as a catalyst for C-C bond formation in various chemical reactions, including Suzuki reaction, Sonogashira coupling, Negishi coupling, and Heck coupling. These reactions are essential for the synthesis of complex organic molecules and have significant applications in the pharmaceutical, agrochemical, and materials science industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Bis(triphenylphosphinepalladium) acetate is used as a catalyst to synthesize various drug molecules and their intermediates. Its ability to facilitate C-C bond formation and its involvement in different coupling reactions make it a valuable tool for the development of new drugs and the improvement of existing ones.
Used in Materials Science:
In the materials science field, Bis(triphenylphosphinepalladium) acetate is used as a catalyst to synthesize advanced materials with specific properties. Its role in C-C bond formation and coupling reactions allows for the creation of novel materials with improved performance in areas such as electronics, energy storage, and polymer science.
Used in the Synthesis of Pyrido[1,2-a]benzimidazole Derivatives:
Bis(triphenylphosphinepalladium) acetate is used as a catalyst in the electro-oxidative intramolecular C-H/N-H annulation reaction to synthesize Pyrido[1,2-a]benzimidazole derivatives. These compounds have potential applications in various fields, including pharmaceuticals and materials science.
Used in the Synthesis of α, β-Unsaturated Carboxylic Acids:
In the chemical synthesis industry, Bis(triphenylphosphinepalladium) acetate is used as a catalyst for the hydroxycarbonylation of vinyl triflates, leading to the formation of α, β-unsaturated carboxylic acids. These acids are important building blocks for the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Synthesis of Secondary Imides:
Bis(triphenylphosphinepalladium) acetate is also used as a catalyst in the C-H functionalization of aldehydes with different N-substituted N-heteroarene-2-carboxamides, resulting in the formation of secondary imides. These compounds have potential applications in the development of new drugs and other chemical products.

InChI:InChI=1/2C18H15P.2C2H4O2.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2*1-2(3)4;/h2*1-15H;2*1H3,(H,3,4);/q;;;;+2/p-2

Upstream product

• 3375-31-3 palladium diacetate 
• 603-35-0 triphenylphosphine 
• 3375-31-3 palladium diacetate 

Downstream Products

• 31989-57-8 bis(triphenylphosphine)palladium⁽⁰⁾ 
• 23604-02-6 cis-[Pd(oxalato)(triphenylphosphine)2] 
• 7440-05-3 palladium 
• 92-52-4 biphenyl 
• 791-28-6 Triphenylphosphine oxide 
• 71-43-2 benzene 
• 28516-49-6 tris(triphenylphosphano)palladium 
• 64-19-7 acetic acid 
• 164071-99-2 [Pd(PPh₃)3(CH₃COO)]^(1-) 
• 17966-74-4 [Pd(O₂CCH₃)2(P(C₆H₅)3)]2 

Relevant articles and documents

Lightly fluorous [Pd(OAc)2{P(C6H4-p-SiMe2CH2CH2C6F13)3}2] in the methoxycarbonylation of styrene: Formation, performance and stability of the catalyst system

The fluorous palladium(II) complex, [Pd(OAc)2{P(C6H4-p-SiMe2CH2CH2C6F13)3}2], has been prepared and characterized. Its application in the catalytic methoxycarbonylation of styrene in an MeOH/CF3C6H5 mixture (1/1 v/v) has been explored and its activity was compared to that of [Pd(OAc)2(PPh3)2]. The fluorous complex showed a lower activity but a significantly higher selectivity towards the branched product. Investigation of both the conversion-versus-time and i:n ratio-versus-time profiles showed an unusual behaviour in the case of the fluorous complex, which has been ascribed to the formation of a dinuclear species for the fluorous complex.

Mechanism of the oxidative carbonylation of terminal alkynes at the ≡C-H bond in solutions of palladium complexes

The formation mechanism of the active catalyst in the oxidative carbonylation of terminal alkynes at the ≡C-H bond has been investigated for the catalytic system Pd(OAc)2-PPh3-p-benzoquinone (Q)-MeOH. It has been demonstrated by NMR spectroscopy, X-ray crystallography, and kinetic measurements that the catalytically active palladium is in the oxidation state 0 and is bound into complexes stabilized by p-benzoquinone (PdL2Q, where L = PPh3). A mechanism is suggested for the catalytic process, which includes the formation of the complex PdL2Q, the oxidative addition of the alkyne to this complex at the ≡C-H bond, the insertion of CO into the Pd-C bond, and steps in which hydride hydrogen is intramolecularly transferred to the p-quinone.

The ubiquitous cross-coupling catalyst system 'Pd(OAc)2'/2PPh3 forms a unique dinuclear PdI complex: An important entry point into catalytically competent cyclic Pd3 clusters

Palladium(ii) acetate 'Pd(OAc)2'/nPPh3 is a ubiquitous precatalyst system for cross-coupling reactions. It is widely accepted that reduction of in situ generated trans-[Pd(OAc)2(PPh3)2] affords [Pd0(PPh3)n] and/or [Pd0(PPh3)2(OAc)]- species which undergo oxidative addition reactions with organohalides-the first committed step in cross-coupling catalytic cycles. In this paper we report for the first time that reaction of Pd3(OAc)6 with 6 equivalents of PPh3 (i.e. a Pd/PPh3 ratio of 1?:?2) affords a novel dinuclear PdI complex [Pd2(μ-PPh2)(μ2-OAc)(PPh3)2] as the major product, the elusive species resisting characterization until now. While unstable, the dinuclear PdI complex reacts with CH2Cl2, p-fluoroiodobenzene or 2-bromopyridine to afford Pd3 cluster complexes containing bridging halide ligands, i.e. [Pd3(X)(PPh2)2(PPh3)3]X, carrying an overall 4/3 oxidation state (at Pd). Use of 2-bromopyridine was critical in understanding that a putative 14-electron mononuclear 'PdII(R)(X)(PPh3)' is released on forming [Pd3(X)(PPh2)2(PPh3)3]X clusters from [Pd2(μ-PPh2)(μ2-OAc)(PPh3)2]. Altering the Pd/PPh3 ratio to 1?:?4 forms Pd0(PPh3)3 quantitatively. In an exemplar Suzuki-Miyaura cross-coupling reaction, the importance of the 'Pd(OAc)2'/nPPh3 ratio is demonstrated; catalytic efficacy is significantly enhanced when n = 2. Employing 'Pd(OAc)2'/PPh3 in a 1?:?2 ratio leads to the generation of [Pd2(μ-PPh2)(μ2-OAc)(PPh3)2] which upon reaction with organohalides (i.e. substrate) forms a reactive Pd3 cluster species. These higher nuclearity species are the cross-coupling catalyst species, when employing a 'Pd(OAc)2'/PPh3 of 1?:?2, for which there are profound implications for understanding downstream product selectivities and chemo-, regio- and stereoselectivities, particularly when employing PPh3 as the ligand.

PROCESS FOR THE PREPARATION OF UNSYMMETRICALLY SUBSTITUTED BIPHENYL COMPOUNDS

A process for the preparation of unsymmetrical biaryl compounds of Formula (I) wherein, R is alkyl, R' is cyano, protected or unprotected tetrazole, or Formula (a) wherein, R" is alkyl, aryl, aralkyl or alkoxy, said process comprising, reacting Grignard reagent of Formula (II) wherein, R is alkyl; X is halogen with an aryl halide of Formula (III) wherein, X is halogen; R' is a cyano, protected or unprotected tetrazole, or Formula (a) wherein, R" is alkyl, aryl, aralkyl or alkoxy in a suitable solvent in the presence of a palladium catalyst and a ligand and Lewis acid as a co catalyst.

Novel imidazole based heterocycles

The present invention is directed to novel imidazopyrazine compounds useful as kinase inhibitors and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, cancers.

Palladium-catalyzed oxidation if triphenylphosphine

In the presence of Pd(II) catalyst, triphenylphosphine can be oxidized with molecular oxygen at room temperature under atmospheric pressure to form triphenylphosphine oxide. The rate of oxidation depended on the type of anionic ligand of palladium salt. The oxidation was inhibited by protic solvents and coordinating solvents such as amine. For palladium acetate as a catalyst, the square planar structure of Pd(OAc)2 (PPh3)]2 was converted into the dimeric structure, [Pd(OAc)2(PPh3)2, as triphenylphosphine was consumed. Finally palladium metal precipitated when triphenylphosphine was oxidized completely. A possible reaction scheme of the Pd(II)-catalyzed oxidation of triphenylphosphine is proposed.

METALLATION OF ALIPHATIC CARBON ATOMS II, SYNTHESES AND CHARACTERIZATION OF THE CYCLOPALLADATED COMPLEXES OF N,N-DIMETHYLNEOPENTYLAMINE

N,N-Dimethyneopentylamine reacts with Pd(MeCO2)2 to give a novel trinuclear cyclopalladated complex *0.5C6H6 (I).The reaction of I with PPh3 affords both trans (III) .The reaction of III with LiCl yields a mononuclear cyclopalladated complex, (IV).