Diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II)
[CAS# 374067-50-2]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: Diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II)
• Synonyms: (R)-Ru(OAc)2(DM-BINAP)
• Molecular Formula: C₅₆H₅₄O₄P₂Ru
• Molecular Weight: 954.04
• CAS Registry Number: 374067-50-2
• EC Number: 844-065-0
• SMILES: CC1=CC(=CC(=C1)P(C2=C(C3=CC=CC=C3C=C2)C4=C(C=CC5=CC=CC=C54)P(C6=CC(=CC(=C6)C)C)C7=CC(=CC(=C7)C)C)C8=CC(=CC(=C8)C)C)C.CC(=O)O.CC(=O)O.[Ru]

Properties

• Melting point: 100 ºC (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H312+H332-H302-H312-H315-H319-H332-H413
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

Diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is a notable compound in the field of organometallic chemistry, particularly for its role in asymmetric catalysis. This ruthenium complex features a chiral ligand that imparts significant catalytic properties and stability, making it valuable in various chemical processes.

The discovery of diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) builds upon the broader exploration of ruthenium-based complexes and their applications in catalysis. The specific focus on the (R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl ligand was driven by the need to develop highly efficient and chiral environments around the ruthenium center. The chiral ligand enhances the complex’s ability to perform asymmetric transformations with high selectivity and efficiency.

The synthesis of this compound involves several stages. The preparation of the (R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl ligand is a critical step, which includes the construction of the binaphthyl backbone and the attachment of di(3,5-xylyl)phosphino groups. Following the synthesis of the ligand, it is combined with a ruthenium precursor and acetate ions to form the diacetato complex. The reaction conditions, including solvent choice, temperature, and reaction time, are carefully controlled to ensure high yield and purity of the final product. The complex is characterized using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and X-ray crystallography to confirm its structure and the presence of the diacetato and phosphine ligands.

One of the primary applications of diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is in asymmetric catalysis. The complex acts as a catalyst or catalyst precursor in various asymmetric reactions, including hydrogenation, oxidation, and other transformations. The (R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl ligand creates an asymmetric environment around the ruthenium center, which significantly enhances the selectivity of these reactions. For example, the complex is used in the asymmetric hydrogenation of ketones and alkenes, where it facilitates the production of chiral products with high enantioselectivity.

In addition to its catalytic applications, diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) is utilized in the synthesis of complex organic molecules. Its ability to facilitate various chemical transformations is valuable in the preparation of pharmaceuticals and fine chemicals. The complex’s stability and reactivity enable the construction of new carbon-carbon and carbon-heteroatom bonds, which are essential for developing intricate molecular structures.

Another area of application for this complex is in materials science. The unique properties of the ruthenium center and the phosphine ligand are exploited to develop new materials with specific characteristics, such as enhanced electronic or optical properties. The complex can be used to prepare ruthenium-based polymers or materials for advanced technologies, including sensors, displays, and electronic devices. The ability of the complex to form stable bonds with various substrates contributes to its utility in these applications.

Despite its advantages, the use of diacetato[(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl]ruthenium(II) poses challenges, such as the need for efficient synthesis and optimization of its catalytic properties. Ongoing research aims to address these challenges by developing more effective synthetic methods and exploring new applications for the complex.

Future research on this compound may focus on expanding its use in emerging fields such as green chemistry and sustainable processes. The complex’s unique properties offer opportunities for innovation in both catalysis and materials science, contributing to advancements in these areas.