14872-20-9

Basic information

• Product Name: DICHLOROBIS(PYRIDINE)PALLADIUM(II)
• Synonyms: DICHLOROBIS(PYRIDINE)PALLADIUM(II);bis(pyridine)palladium(ii) chloride;Dichlorobis(pyridine)palladium(Ⅱ);Nsc180812;Palladium pyridine chloride;Palladium, dichlorobis(pyridine)-
• CAS NO: 14872-20-9
• Molecular Formula: C₁₀H₁₀Cl₂N₂Pd
• Molecular Weight: 335.53
• Mol File: 14872-20-9.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 106.4°Cat760mmHg
• Flash Point: 4.4°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 22.8mmHg at 25°C
• CAS DataBase Reference: DICHLOROBIS(PYRIDINE)PALLADIUM(II)(CAS DataBase Reference)
• NIST Chemistry Reference: DICHLOROBIS(PYRIDINE)PALLADIUM(II)(14872-20-9)
• EPA Substance Registry System: DICHLOROBIS(PYRIDINE)PALLADIUM(II)(14872-20-9)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-36/37/39
• Hazardous Substances Data: 14872-20-9(Hazardous Substances Data)

Usage

General Description

DICHLOROBIS(PYRIDINE)PALLADIUM(II) is a chemical compound composed of a palladium ion bonded to two chloride ions and two pyridine molecules. It is a coordination complex that is commonly used in organic synthesis as a catalyst for various reactions, including C-C cross-coupling reactions and carbonylation reactions. DICHLOROBIS(PYRIDINE)PALLADIUM(II) is a valuable tool in the field of organic chemistry, as it enables the formation of complex organic molecules with high selectivity and efficiency. It is known for its high stability and reactivity, making it a versatile and valuable reagent in chemical research and industrial processes.

InChI:InChI=1/2C5H5N.2ClH.Pd/c2*1-2-4-6-5-3-1;;;/h2*1-5H;2*1H;/q;;;;+2/p-2

Upstream product

• 110-86-1 pyridine 
• 13750-62-4 N-benzyl-2-methylimidazole 
• 78-95-5 chloroacetone 
• 935544-87-9 HCN(CH₂C(O)NHC₆H₅)CHCHN(CH₂C(O)NHC₆H₅)⁽¹⁺⁾*Cl^(1-)=(HCN(CH₂C(O)NHC₆H₅)CHCHN(CH₂C(O)NHC₆H₅))Cl 
• 78610-10-3 Pd₂Cl₄(As(C(CH₃)3)3)2 
• 59245-57-7 tetrapyridine palladium (II) tetrachloropalladate (II) 
• 1121-60-4 pyridine-2-carbaldehyde 
• 7440-05-3 palladium 
• 40691-28-9 PdCl₂(P(C₆H₅)(2-C₆H₄Cl)2)2 
• 100898-99-5 bis(μ-chloro)bis[1-3-η3-(1-chloromethyl)-1-buten-3-yl]dipalladium(II) 

Downstream Products

• 54845-69-1 cis-[Pd(C₆F₅)2(py)2] 
• 134625-37-9 PdCl₂(PPh₃)(py) 
• 6894-19-5 bis(aniline)dichloridopalladium(II) 
• 632326-76-2 cis-[Pd(CH₂Ph)2(pyridine)2] 
• 13815-17-3 tetramminepalladium(II) chloride 

Relevant articles and documents

Synthesis and characterization of novel PEPPSI type bicyclic (alkyl)(amino)carbene (BICAAC)-Pd complexes

A series of bicyclic alkylamino carbenes (BICAAC) (where N-aryl = dipp, mes, 2,6-dimethyl-4-(dimethylamino)phenyl, 5a–d) and their novel air- and moisture-resistant pyridine (pyridine, 4-dimethylaminopyridine) containing palladium Pd(II) complexes (6a–e) were synthetized and characterized. As novel examples of the PEPPSI (“pyridine enhanced precatalyst preparation stabilization and initiation”)-Pd compounds, the reported complexes have shown high activity in Mizoroki–Heck coupling reaction even at as low as 100 ppm loading (TON up to 10000). Kinetic studies revealed that reactions carried out in the presence of elemental mercury resulted decrease in activity. It indicates that the coupling reaction may have both molecular and Pd(0)-mediated catalytic paths.

Understanding existing and designing novel synthetic routes to Pd-PEPPSI-NHC and Pd-PEPPSI-PR3pre-catalysts

The reaction mechanism leading to the formation of cross-coupling palladium pre-catalysts of the PEPPSI family was investigated. Two intermediates were isolated and proved to be both suitable synthons to the pre-catalysts, with one permitting the design of a novel and greener user-friendly synthetic route. In light of this mechanistic understanding, the traditional one-pot method was shown to be possible using stoichiometric amounts of throw-away ligand, which represents a considerable synthetic improvement over the wasteful “in pyridine” approach.

Synthesis and catalytic application of Pd complex catalysts: Atom-efficient cross-coupling of triarylbismuthines with haloarenes and acid chlorides under mild conditions

Palladium-catalysed cross-coupling reactions are some of the most frequently used synthetic tools for the construction of new carbon–carbon bonds in organic synthesis. In the work presented, Pd(II) complex catalysts were synthesized from palladium chloride and nitrogen donor ligands as the precursors. Infrared and 1H NMR spectroscopic analyses showed that the palladium complexes were formed in the bidentate mode to the palladium centre. The resultant Pd(II) complexes were tested as catalysts for the coupling of organobismuth(III) compounds with aryl and acid halides leading to excellent yields with high turnover frequency values. The catalysts were stable under the reaction conditions and no degradation was noticed even at 150°C for one of the catalysts. The reaction proceeds via an aryl palladium complex formed by transmetallation reaction between catalyst and Ar3Bi. The whole synthetic transformation has high atom economy as all three aryl groups attached to bismuth are efficiently transferred to the electrophilic partner.