525602-71-5

Basic information

• Product Name: chloro-bis-(2,4-bis-(trifluoromethyl)-phenyl)-phosphane
• Synonyms: chloro-bis-(2,4-bis-(trifluoromethyl)-phenyl)-phosphane
• CAS NO: 525602-71-5
• Molecular Weight: 492.631
• Mol File: 525602-71-5.mol

Chemical Properties

• CAS DataBase Reference: chloro-bis-(2,4-bis-(trifluoromethyl)-phenyl)-phosphane(CAS DataBase Reference)
• NIST Chemistry Reference: chloro-bis-(2,4-bis-(trifluoromethyl)-phenyl)-phosphane(525602-71-5)
• EPA Substance Registry System: chloro-bis-(2,4-bis-(trifluoromethyl)-phenyl)-phosphane(525602-71-5)

Safety Data

• Hazardous Substances Data: 525602-71-5(Hazardous Substances Data)

Upstream product

• 1039309-32-4 bis[2,4-bis(trifluoromethyl)phenyl]diethylaminophosphane 

Downstream Products

• 1072140-76-1 C₃₂H₁₂F₂₄OP₂ 
• 1072140-77-2 C₃₂H₁₂F₂₄OP₂ 
• 1039309-37-9 bis[2,4-bis(trifluoromethyl)phenyl]phosphane oxide 

Relevant articles and documents

Investigations of the tautomeric equilibria between phosphane oxides and their corresponding phosphinous acids bearing electron-withdrawing perfluoroaryl groups

The unusual form of a phosphinous acid can be stabilized by strongly electron-withdrawing substituents such as trifluoromethyl and pentafluoroethyl groups. The less electron-withdrawing pentafluorophenyl group favors the phosphane oxide tautomer (Rf)2P(O)H in the solid state, whereas in solution a solvent-dependent equilibrium with the phosphinous acid tautomer (Rf)2POH is observed. The increasing donating ability of the solvent leads to an increasing amount of the corresponding phosphinous acid tautomer. In accord with quantum chemical calculations, the electron-withdrawing effects of the p-tetrafluoropyridyl and 2,4-bis(trifluoromethyl)phenyl groups exceed the pentafluorophenyl group and should therefore be ideally suited to stabilize the corresponding phosphinous acid tautomer (Rf)2POH. The syntheses of bis(tetrafluoropyridyl)- and bis[2,4-bis(trifluoromethyl)phenyl]phosphane oxide enabled the investigation of the solvent-dependent tautomerism by NMR spectroscopy. Introduction of the tetrafluoropyridyl group shifts the tautomeric equilibrium significantly towards the phosphinous acid. Surprisingly, the comparably electron-withdrawing but more bulky 2,4-bis(trifluoromethyl)phenyl group favors the oxide tautomer. The experimental results have been confirmed by DFT calculations. In summary, electron-withdrawing substituents stabilize the phosphinous acid tautomer, whereas it is destabilized by space-demanding groups by an increased C-P-C angle. The solvent-dependent tautomeric equilibria between secondary phosphane oxides and their corresponding phosphinous acids bearing electron-withdrawing fluoroaryl groups is reported. Copyright

Tetrakis[2,4-bis(trifluoromethyl)phenyl]diphosphoxane: An anhydride of a phosphinous acid

Steric and electronic characteristics of the bulky, strongly electron-withdrawing 2,4-(CF3)2C6H3 group are ideally suited to stabilize the unusual form of a diphosphoxane, R2POPR2, the anhydride of a phosphinous acid. The high-yield synthesis and first structural characterization of a tetraorganyl diphosphoxane are described (see structure; C gray, H white, O red, F yellow, P green). (Figure Presented)