Dichloro(1,5-cyclooctadiene)palladium(II) CAS 12107-56-1

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Dichloro(1,5-cyclooctadiene)palladium(II), bearing the molecular formula C₈H₁₂Cl₂Pd and CAS registry number 12107-56-1, is a core transition metal organometallic compound that plays an irreplaceable and crucial catalytic role in various branches of modern fine chemical synthesis and cross-coupling catalytic reactions. It typically appears as a distinctive yellow solid; rather than a bright, vivid lemon yellow, its hue is a deep, warm amber‑like tone with a subtle metallic luster visible under ambient laboratory lighting. The raw material is commonly encountered in the form of uniform fine crystals or a dry free‑flowing powder, whose delicate loose texture ensures exceptional ease of accurate weighing, air-sensitive transfer, and safe routine handling under standard inert laboratory conditions.

This palladium complex exhibits extremely poor solubility in all aqueous media and is essentially completely insoluble in pure water and dilute aqueous solutions. However, it dissolves readily and completely in a wide range of polar and nonpolar organic solvents, including anhydrous dichloromethane, glacial acetic acid, chloroform and toluene. This unique solubility profile greatly expands its practical utility in complex organic synthesis and homogeneous catalysis, as it can be conveniently and uniformly introduced into homogeneous liquid-phase reaction systems by selecting matching appropriate reaction solvents, thereby enabling high-efficiency, mild and highly selective catalytic molecular transformation processes.

Dichloro(1,5-cyclooctadiene)palladium(II), as an important organometallic compound, has wide exertion in the domain of chemistry. Its unique structure and properties have shown strong potential in various domain such as organic synthesis, catalytic reactions, and materials science.

Carbon carbon bond formation reaction

Palladium (1,5-cyclooctadiene) dichloride exhibits excellent catalytic performance in the formation of carbon carbon bonds. This type of reaction is one of the key steps in constructing complex organic molecular structures and is of great significance for synthesizing compounds with specific functions. For example, the formation of carbon carbon bonds is an essential step in the synthesis of complex molecules with biological activity.

Carbon nitrogen bond formation reaction

In addition to the formation of carbon carbon bonds, (1,5-cyclooctadiene) palladium dichloride can also catalyze the formation of carbon nitrogen bonds. This type of reaction is of great significance in the synthesis of nitrogen-containing organic compounds, as it can synthesize compounds with specific functional groups, providing more possibilities for drug synthesis and materials science

The pore structure of MOF has a significant impact on its performance. By regulating the pore size, shape, and distribution of MOFs, precise control of their properties can be achieved. Dichloro-1,5-cyclooctadiene palladium (II) as a catalyst can affect the coordination reaction during MOF synthesis, thereby regulating its pore structure.For example, when synthesizing MOFs with large pores, introducing dichloro (1,5-cyclooctadiene) palladium (II) as a catalyst can promote the coordination reaction between metal ions and organic ligands, forming MOF materials with large pores. This material has potential exertion value in gas adsorption and separation, catalysis, and other domain.

Regulating the pore structure of MOFs 

The chemical stability of MOFs is one of the key factors affecting their exertion performance. By optimizing the chemical stability of MOFs, their service life can be extended and their application performance in various environments can be improved.

Dichloro-1,5-cyclooctadiene palladium (II) as a catalyst can affect the formation and cleavage of chemical bonds during MOF synthesis, thereby optimizing its chemical stability.

Optimize the chemical stability of MOF

 

For example, when synthesizing MOFs with excellent chemical stability, introducing dichloro (1,5-cyclooctadiene) palladium (II) as a catalyst can promote the formation of chemical bonds between metal ions and organic ligands, forming MOF materials with excellent chemical stability. This material has broad exertion  prospects in domain such as catalysis and sensing.

Overview of Chemical Structure 

The chemical formula of dichloro (1,5-cyclooctadiene) palladium (II) is C8H12Cl2Pd, with a molecular weight of 285.507 (exact mass may vary slightly). The key elements in its structure include palladium (Pd), chlorine (Cl), carbon (C), and hydrogen (H), which are connected together through specific chemical bonds to form molecules with specific geometric configurations.

Palladium atom

The palladium atom is located at the center of the molecule and is the central metal ion of the complex. In this substance, palladium atoms exhibit a+2 valence state, which means they have lost two electrons and formed two positive charges.These two positive charges are balanced through coordination bonds with ligands and chloride ions.

Ligand

1,5-Cyclooctadiene is the ligand for this substance. A ligand is a molecule or ion that can form a coordination bond with a central metal ion. In 1,5-cyclooctadiene, two double bonds (C=C) connect eight carbon atoms into a cyclic structure. This structure enables 1,5-cyclooctadiene to form stable coordination bonds with palladium atoms.

Chloride ions

In addition to the ligand, it also contains two chloride ions. Chloride ions, as anions, form coordination bonds with palladium atoms, thereby stabilizing the structure of the complex.

Coordination characteristics

Coordination properties are key parameters that describe the interaction between the central metal ion and the ligand in a complex. In this substance, coordination properties mainly involve the formation of coordination bonds, coordination numbers, and geometric configurations.

Formation of coordination bonds

 

Coordination bond is a chemical bond formed between the central metal ion and the ligand. In this substance, coordination bonds are formed between palladium atoms, carbon atoms of 1,5-cyclooctadiene, and chloride ions. These coordination bonds are formed through the sharing or transfer of electrons, thereby stabilizing the structure of the complex.

 

Specifically, the d orbital electrons of palladium atoms can form π - d coordination bonds with the π orbital electrons of 1,5-cyclooctadiene. This coordination bond has a high bond energy, making the complex highly stable in solution. Meanwhile, palladium atoms can also form sigma coordination bonds with the p-orbital electrons of chloride ions, further enhancing the stability of the complex.

Coordination number

 

Coordination number refers to the number of ligands or ions around the central metal ion that coordinate with it. In this substance, the coordination number of palladium atoms is 4. This means that there are four ligands around the palladium atom, two of which are carbon atoms of 1,5-cyclooctadiene, and the other two are chloride ions.

 

Coordination number refers to the number of ligands or ions around the central metal ion that coordinate with it. In this substance, the coordination number of palladium atoms is 4. This means that there are four ligands around the palladium atom, two of which are carbon atoms of 1,5-cyclooctadiene, and the other two are chloride ions.

Geometric configuration

Geometric configuration refers to the relative spatial arrangement between the central metal ion and the ligand in a complex. The palladium atom forms a tetrahedral geometric configuration with four ligands. Tetrahedral geometry is a very common complex geometry. In this configuration, the central metal ion is located at the center of the tetrahedron, while the four ligands are located at the four vertices of the tetrahedron. This configuration gives the complex a high degree of symmetry and stability in solution.Specifically, the palladium atom is located at the center of the tetrahedron, while the carbon atoms of two 1,5-cyclooctadienes and two chloride ions are located at the four vertices of the tetrahedron, respectively. This arrangement allows the complex to maintain a stable structure and properties in solution.

Dichloro(1,5-cyclooctadiene)palladium(II),The chemical formula is C8H12Cl2Pd, which is an important organometallic compound with wide exertion in chemical synthesis, materials science, and catalysis. Its unique structure and properties play a crucial role in catalyzing the formation of C-C and C-N bonds, particularly in cross coupling reactions such as Heck coupling and Suzuki coupling. Here are its development prospects:

► Environmental friendliness and sustainable development

► Policy support and international cooperation

Guidance and support from government policies

The government plays an important role in promoting the development of this industry. By formulating relevant industrial policies, providing financial support, and strengthening intellectual property protection measures, enterprises can be guided to increase research and development investment, improve product quality, and enhance market competitiveness.

 

Strengthening international cooperation

 

With the continuous deepening of globalization, international cooperation plays an increasingly important role in promoting the development of this industry. By strengthening cooperation and exchanges with international advanced enterprises and research institutions, advanced technology and management experience can be introduced, international markets can be expanded, and international competitiveness can be improved.

The formulation and adherence to international standards

In order to promote the standardized development of this industry, it is necessary to formulate and improve relevant international standards. These standards can include product quality standards, environmental standards, safety standards, etc. By following these standards, it can be ensured that the industry develops on a healthy and safe track.

Safety and Handling

Dichloro(1,5-cyclooctadiene)palladium(II) ([PdCl₂(COD)]) requires careful handling due to the inherent health risks associated with palladium-based compounds.

Palladium salts may pose toxicity risks through ingestion, inhalation, or dermal absorption, necessitating strict safety protocols during use. It is imperative to wear proper personal protective equipment-including chemical-resistant gloves, safety goggles, and a laboratory coat-when handling this substance. For storage, [PdCl₂(COD)] should be kept in a cool, dry, well-ventilated area, isolated from heat sources, sparks, and open flames. In the event of a spill, established decontamination and cleanup procedures must be followed, and the waste material should be disposed of in compliance with local environmental regulations.

references

Anderson C B, Burreson B J, Michałowski J. Methanolysis Products of Dichloro(1,5-cyclooctadiene)palladium(II) in the Presence of Bases and of Its Methoxy Adducts[J]. Inorganic Chemistry, 1976, 15(10): 2487-2491. DOI:10.1021/ic50164a034

Fairlamb I J S. Solvent coordination to palladium can invert the selectivity of oxidative addition[J]. Chemical Science, 2021, 12(9): 2936-2948. DOI:10.1039/D0SC06214A

Biscoe M R, Fors B P, Buchwald S L. A New Class of Easily Activated Palladium Precatalysts for Cross-Coupling Reactions[J]. Journal of the American Chemical Society, 2008, 130(24): 7838-7839. DOI:10.1021/ja802486t

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