5075-61-6

Usage

Uses

Used in Organometallic Chemistry and Catalysis:
(Pentafluorophenyl)dimethylphosphine is used as a ligand in organometallic chemistry and catalysis, enhancing the efficiency and selectivity of various chemical reactions.
Used in Pharmaceutical Industry:
(Pentafluorophenyl)dimethylphosphine is utilized in the synthesis of various organic compounds, contributing to the development of new pharmaceutical products due to its unique reactivity.
Used in Materials Science:
(Pentafluorophenyl)dimethylphosphine is also employed in materials science, where its properties and reactivity are harnessed for the creation of novel materials with specific characteristics.
Used in Chemical Reactions as a Reagent:
(Pentafluorophenyl)dimethylphosphine serves as a reagent in chemical reactions, facilitating the synthesis of a wide range of organic compounds, which are essential for various applications across different industries.

Upstream product

• 392-56-3 Hexafluorobenzene 
• 3676-91-3 tetramethyldiphosphane 
• 26464-99-3 dimethyl(trimethylsilyl)phosphine 
• 5032-91-7 pentafluorophenyl dichlorophosphine 
• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 21743-25-9 lithium dimethylphosphide 

Downstream Products

• 80431-26-1 Trimethyl(pentafluorphenyl)phosphoniumbromid 
• 80431-27-2 Trimethyl(pentafluorphenyl)phosphoniumiodid 
• 80431-29-4 Dimethylmethylen(pentafluorphenyl)phosphoran 
• 19100-54-0 Dimethyl(pentafluorophenyl)phosphane sulfide 

Relevant academic research and scientific papers

Trimethylsilyl- and trimethylstannyldimethylphosphane - Convenient and versatile reagents for the synthesis of polyfluoroaryldimethylphosphanes

Trimethylsilyldimethylphosphane (Me3SiPMe2) and the corresponding tin compound (Me3SnPMe2) were used as reagents for the substitution of fluorine by the Me2P group in polyfluoroarenes C6F5X (X = F, H, Cl, CF3) and C5NF5. The reactions occur even under mild conditions (T= 0-20°C), either in benzene or without solvent, to give as a rule 4-X-1-(dimethylphosphano)tetrafluorobenzenes (XC6F4PMe2, 1-4) and 4-(dimethylphosphano)tetrafluoropyridine (C5NF4PMe2, 5), respectively, in yields between 75 and 95 %. In the case of C6F6, double substitution is also observed, which affords 1,4-bis(dimethylphosphano)tetrafluorobenzene (6). A very efficient route to the compounds XC6F4PMe2 (X=F, H, Cl, CF3) and C5NF4PMe2 was developed as a one-pot reaction of the corresponding fluoroarenes with tetramethyldiphosphane (P2Me4) and trimethyltin hydride (Me3SnH) at moderate temperatures. This process was tested for C6F6 and perfluorobiphenyl which gave C6F5PMe2 (1) and 4,4′-bis(dimethylphosphano)octafluorobiphenyl (7), respectively. The results, which included kinetic measurements that used the intensities of the 31P signals, revealed the influence of the substrate type on the rate of reaction in the sequence: C5NF5 > C6F5CF3 > C6F5Cl, C6F5PMe2 > C6F5H > C6F6? C6H5F. Ab initio calculations were carried out on the model reactions of pentafluoropyridine with silylphosphane, phosphane or phosphide to discriminate between possible reaction mechanisms. The novel phosphanes were characterised by spectroscopic investigations (NMR, MS), by preparation of the related thiophosphanes ArFP(=S)Me2 (8-14), their spectroscopic and analytic data and single crystal X-ray diffraction studies on five of these derivatives.