Bis(diphenylphosphino)methane
[CAS# 2071-20-7]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Bis(diphenylphosphino)methane
• Synonyms: Methylenebis(diphenylphosphine); DPM
• Molecular Formula: C₂₅H₂₂P₂
• Molecular Weight: 384.40
• CAS Registry Number: 2071-20-7
• EC Number: 218-194-2
• SMILES: C1=CC=C(C=C1)P(CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

Properties

• Melting point: 118-122 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Bis(diphenylphosphino)methane is an important chemical compound in the field of organophosphorus chemistry, known for its unique structure and wide range of applications. This compound features a central methane group bonded to two diphenylphosphine groups, creating a molecule with significant potential in various chemical processes and research areas.

The discovery of bis(diphenylphosphino)methane can be traced back to the exploration of phosphine ligands in coordination chemistry. The synthesis of this compound involves the reaction of diphenylphosphine with a suitable methane derivative, often under controlled conditions to ensure the formation of the desired product. The resulting compound exhibits a highly symmetrical structure, with the central methane group providing a platform for the two diphenylphosphine groups to coordinate with metal centers or participate in other chemical reactions.

One of the primary applications of bis(diphenylphosphino)methane is in the field of catalysis. This compound acts as a versatile ligand in various metal-catalyzed reactions, including hydrogenation, hydroformylation, and cross-coupling reactions. The diphenylphosphine groups in bis(diphenylphosphino)methane can effectively coordinate with metal centers, influencing their electronic properties and reactivity. This interaction enhances the efficiency and selectivity of catalytic processes, making it a valuable tool in both academic research and industrial applications.

In addition to its role in catalysis, bis(diphenylphosphino)methane is also used in the development of advanced materials. Its ability to form stable complexes with transition metals makes it useful in the synthesis of organometallic compounds and coordination polymers. These materials have potential applications in various fields, including electronics, photonics, and materials science. For example, the coordination of bis(diphenylphosphino)methane with metal centers can lead to the formation of novel materials with unique optical and electronic properties, which are valuable in the development of advanced electronic devices and sensors.

The study of bis(diphenylphosphino)methane also contributes to the broader understanding of ligand design and metal-ligand interactions. Researchers use this compound to investigate the effects of different phosphine ligands on the reactivity and stability of metal complexes. By exploring the properties of bis(diphenylphosphino)methane and its derivatives, scientists gain insights into the principles of coordination chemistry and the design of more effective catalysts and materials.

Overall, the discovery and applications of bis(diphenylphosphino)methane highlight its significance in various chemical processes and research areas. Its role as a versatile ligand in catalysis and materials development underscores its value in advancing both fundamental chemistry and practical applications.

References

2023. Dinuclear Reactivity Between the Two Metal Centers. Modes of Cooperative Effects in Dinuclear Complexes.
DOI: 10.1007/3418_2023_88

2022. Ruthenafuran Complexes Supported by the Bipyridine-Bis(diphenylphosphino)methane Ligand Set: Synthesis and Cytotoxicity Studies. Molecules (Basel, Switzerland), 27(5).
DOI: 10.3390/molecules27051709

1965. Spectra and structure of salts of organophosphorus compounds salts containing the diphosphinomethyne group. Journal of Structural Chemistry, 6(5).
DOI: 10.1007/bf00747098