Dichloro(p-cymene)ruthenium(II) dimer
[CAS# 52462-29-0]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Dichloro(p-cymene)ruthenium(II) dimer
• Molecular Formula: C₂₀H₂₈Cl₄Ru₂
• Molecular Weight: 612.39
• CAS Registry Number: 52462-29-0
• EC Number: 435-530-5
• SMILES: CC1=CC=C(C=C1)C(C)C.CC1=CC=C(C=C1)C(C)C.Cl[Ru]Cl.Cl[Ru]Cl

Properties

• Melting point: 250 °C (dec.)
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H302-H319-H331-H341-H361-H412
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P304+P340-P305+P351+P338-P316-P318-P321-P330-P337+P317-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Dichloro(p-cymene)ruthenium(II) dimer is a significant chemical compound in the field of organometallic chemistry and catalysis. This complex, commonly denoted as [RuCl₂(p-cymene)]₂, features a ruthenium(II) center coordinated with two chlorides and one p-cymene ligand per ruthenium atom, and it forms a dimeric structure. Its discovery and subsequent applications highlight its role as a versatile and efficient catalyst in various chemical transformations.

The synthesis of Dichloro(p-cymene)ruthenium(II) dimer involves the reaction of ruthenium(II) chloride with p-cymene, a common ligand in organometallic chemistry. The preparation typically requires the use of inert atmosphere conditions to prevent oxidation or other side reactions. The dimeric nature of the complex arises from the bridging of two ruthenium centers by chlorides, which stabilizes the structure and enhances its catalytic properties.

In terms of structure, the compound consists of two ruthenium atoms each coordinated to one p-cymene ligand and two chloride ions. The p-cymene ligand, a substituted aromatic compound, provides a stable coordination environment around the ruthenium centers. This arrangement contributes to the overall stability and reactivity of the complex. The dimeric form of the compound allows for unique interactions with substrates and reagents during catalytic processes.

The primary application of Dichloro(p-cymene)ruthenium(II) dimer is in the field of catalysis. This compound is employed as a catalyst in a variety of chemical reactions, particularly those involving C-H activation and functionalization. Its effectiveness in these reactions stems from its ability to facilitate the formation of new carbon-carbon and carbon-heteroatom bonds through catalytic cycles involving oxidative addition and reductive elimination steps.

One notable application of this complex is in the dehydrogenation of alkanes and alcohols. Dichloro(p-cymene)ruthenium(II) dimer catalyzes the removal of hydrogen from these substrates, producing alkenes or ketones, respectively. This reaction is valuable in organic synthesis for the formation of unsaturated compounds and can be employed in the production of various chemicals and pharmaceuticals.

Additionally, the compound has been used in cross-coupling reactions, where it helps to form carbon-carbon bonds between different organic molecules. This application is important for the synthesis of complex organic compounds, including pharmaceuticals and materials with specific properties. The ability of Dichloro(p-cymene)ruthenium(II) dimer to facilitate such reactions makes it a valuable tool in both academic and industrial settings.

In the field of homogeneous catalysis, Dichloro(p-cymene)ruthenium(II) dimer is also utilized in the activation of C-H bonds in hydrocarbons. This process is significant for the functionalization of otherwise inert C-H bonds, allowing for the introduction of functional groups into complex organic molecules. The ability to selectively activate and functionalize these bonds is a key aspect of the compound's utility in synthetic chemistry.

Handling and storage of Dichloro(p-cymene)ruthenium(II) dimer require careful attention to maintain its stability. The compound should be stored in a cool, dry environment, protected from light and moisture. Proper handling techniques are essential to avoid degradation and ensure the efficacy of the complex in catalytic applications.

Future research on Dichloro(p-cymene)ruthenium(II) dimer may focus on expanding its applications in new catalytic processes and exploring its interactions with various substrates. Advances in the understanding of its reactivity and mechanisms could lead to the development of more efficient and selective catalytic systems.

References

2023. Recent advances in ruthenium-catalyzed reactions: A review. Science China Chemistry, 66(8).
DOI: 10.1007/s11426-022-1541-5

2022. Synthesis and catalytic applications of dichloro(p-cymene)ruthenium(II) dimer. Russian Journal of General Chemistry, 92(12).
DOI: 10.1134/s107036322212043x

2001. Catalytic properties of ruthenium complexes in organic synthesis. Catalysis Letters, 73(2).
DOI: 10.1023/a:1016643711546