1,1'-Bis((R)-(dimethylamino)(phenyl)methyl)ferrocene
[CAS# 174589-08-3]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic iron
• Name: 1,1'-Bis((R)-(dimethylamino)(phenyl)methyl)ferrocene
• Molecular Formula: C₂₈H₃₂FeN₂
• Molecular Weight: 452.41
• CAS Registry Number: 174589-08-3
• SMILES: CN(C)C(C1=C[CH-]C=C1)C2=CC=CC=C2.CN(C)C(C1=C[CH-]C=C1)C2=CC=CC=C2.[Fe+2]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P262-P280-P305+P351+P338-P304+P340-P403+P233-P501

Discovory and Applicatios

1,1'-Bis((R)-(dimethylamino)(phenyl)methyl)ferrocene, commonly abbreviated as BDPF, is a notable compound in the realm of organometallic chemistry and catalysis. This compound integrates the ferrocene structure with two bulky substituents, including a dimethylamino group and a phenyl group, attached to the central ferrocene unit. This unique structure imparts distinctive electronic and steric properties to BDPF, making it a valuable reagent in various chemical applications.

The discovery of BDPF is linked to advancements in the development of organometallic ligands and catalysts. Ferrocene, a well-known metallocene, serves as the backbone of BDPF. The ferrocene structure, consisting of two cyclopentadienyl rings sandwiching an iron atom, is renowned for its stability and versatile reactivity. Researchers sought to enhance the reactivity and selectivity of ferrocene-based compounds by introducing functional groups that could interact with transition metals and other substrates.

The synthesis of BDPF involves the introduction of two (R)-(dimethylamino)(phenyl)methyl groups onto the ferrocene core. The (R)-dimethylamino group provides a strong donor effect, which can influence the electronic properties of the ferrocene ring. The phenyl groups add steric bulk, which can affect the spatial arrangement of the substituents and the overall geometry of the molecule. The combination of these groups results in a compound with unique properties that can be tailored for specific applications.

One of the primary applications of BDPF is in the field of asymmetric catalysis. Asymmetric catalysis involves the use of chiral catalysts to produce enantiomerically pure compounds, which are essential in the pharmaceutical and fine chemicals industries. BDPF, with its chiral centers and unique electronic environment, is employed as a ligand in asymmetric catalysis to facilitate the formation of chiral products with high selectivity.

In particular, BDPF has been used as a ligand in asymmetric hydrogenation reactions. Hydrogenation, the addition of hydrogen to unsaturated compounds, is a critical process in organic synthesis. By coordinating with transition metals, BDPF enhances the reactivity of the metal centers and improves the selectivity of the reaction. This application is significant for the synthesis of chiral alcohols, amines, and other valuable compounds.

Another notable application of BDPF is in catalytic C-H activation reactions. C-H activation is a process where carbon-hydrogen bonds in organic molecules are selectively cleaved and functionalized. BDPF, as a ligand, plays a role in stabilizing the transition metal complexes involved in these reactions, facilitating the activation and transformation of C-H bonds. This application is important for the development of new synthetic methodologies and the functionalization of complex organic molecules.

BDPF also finds utility in materials science. Its ferrocene backbone and functional groups allow it to be incorporated into polymer matrices or used as a modifier for surfaces. The ability to fine-tune the electronic and steric properties of BDPF makes it a candidate for creating novel materials with tailored properties, such as enhanced conductivity or specific reactivity.

The synthesis of BDPF is achieved through a series of chemical reactions starting with ferrocene. The process involves the selective introduction of the (R)-(dimethylamino)(phenyl)methyl groups onto the ferrocene core. This typically requires the use of protecting groups, careful control of reaction conditions, and purification steps to ensure the formation of high-purity BDPF. Characterization techniques such as nuclear magnetic resonance (NMR) spectroscopy and X-ray crystallography are employed to confirm the structure and purity of the final product.

In summary, 1,1'-Bis((R)-(dimethylamino)(phenyl)methyl)ferrocene is a versatile compound with significant applications in asymmetric catalysis, C-H activation, and materials science. Its discovery and development have provided valuable tools for organic synthesis and the creation of advanced materials. The unique properties of BDPF, arising from its ferrocene backbone and functional substituents, continue to drive research and innovation in various fields of chemistry.