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

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Identification
ClassificationOrganic raw materials >> Organic phosphine compound
NameBis(diphenylphosphino)methane
SynonymsMethylenebis(diphenylphosphine); DPM
Molecular StructureCAS # 2071-20-7, Bis(diphenylphosphino)methane
Molecular FormulaC25H22P2
Molecular Weight384.40
CAS Registry Number2071-20-7
EC Number218-194-2
SMILESC1=CC=C(C=C1)P(CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
Properties
Melting point118-122 °C
Safety Data
Hazard Symbolssymbol   GHS07 Warning  Details
Risk StatementsH315-H319-H335  Details
Safety StatementsP261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Skin irritationSkin Irrit.2H315
SDSAvailable
up Discovery and Applications
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
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