13406-27-4

Basic information

• Product Name: Phosphine oxide, tris[4-(trifluoromethyl)phenyl]-
• CAS NO: 13406-27-4
• Molecular Formula: C21H12F9OP
• Molecular Weight: 482.285
• Mol File: 13406-27-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Phosphine oxide, tris[4-(trifluoromethyl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphine oxide, tris[4-(trifluoromethyl)phenyl]-(13406-27-4)
• EPA Substance Registry System: Phosphine oxide, tris[4-(trifluoromethyl)phenyl]-(13406-27-4)

Safety Data

• Hazardous Substances Data: 13406-27-4(Hazardous Substances Data)

Upstream product

• 1366181-69-2 [(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdMe(OP(p-CF3C6H4)3)] 
• 603-35-0 triphenylphosphine 
• 13406-29-6 tris(para-trifluoromethyl)phenyl phosphine 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 13406-26-3 4-Dimethylamino-N--anilin 

Downstream Products

• 1366181-69-2 [(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdMe(OP(p-CF3C6H4)3)] 
• 15929-43-8 bis(4-(trifluoromethyl)phenyl)phosphine oxide 
• 1449430-76-5 (E)-[2-(1,2-diphenylethenyl)-4-(trifluoromethyl)phenyl]bis-[4-(trifluoromethyl)phenyl]phosphine oxide 
• 13406-29-6 tris(para-trifluoromethyl)phenyl phosphine 

Relevant articles and documents

Chemistry of singlet oxygen with arylphosphines

The chemistry of singlet oxygen with a variety of arylphosphines has been studied. Rates of singlet oxygen removal by para-substituted arylphosphines show good correlation with the Hammett σ parameter (ρ=-1.53 in CDCl3), and with the Tolman electronic parameter. The only products for the reactions of these phosphines with singlet oxygen are the corresponding phosphine oxides. Conversely, for ortho-substituted phosphines with electron-donating substituents, there are two products, namely a phosphinate formed by intramolecular insertion and phosphine oxide. Kinetic analyses demonstrate that both products are formed from the same intermediate, and this allows determination of the rate ratios for the competing pathways. Increasing the steric bulk of the phosphine leads to an increase in the amount of insertion product. VT NMR experiments show that peroxidic intermediates can only be detected for very hindered and very electron-rich arylphosphines.

THE SYNTHESIS OF TRIS-(TRIFLUOROMETHYLPHENYL)PHOSPHINES AND PHOSPHINE OXIDES

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The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

Ir(III)-catalyzed direct C-H functionalization of arylphosphine oxides: A strategy for MOP-type ligands synthesis

Diazo compounds as coupling partners are efficiently applied to Ir(III)-catalyzed direct C-H functionalization of arylphos-phine oxides. Involving C-H activation, carbene insertion, and tautomerism, this reaction proceeds under mild conditions, thus proving an approach to the synthesis of MOP-type ligand precursor in a single step. The utility of this transformation has been further demonstrated in ligand synthesis as well as in the construction of phosphole framework.