315190-38-6

Basic information

• Product Name: 4-(diphenylphosphinyl)-2,3,5,6-tetrafluoropyridine
• Synonyms: 4-(diphenylphosphinyl)-2,3,5,6-tetrafluoropyridine
• CAS NO: 315190-38-6
• Molecular Weight: 335.24
• Mol File: 315190-38-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-(diphenylphosphinyl)-2,3,5,6-tetrafluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(diphenylphosphinyl)-2,3,5,6-tetrafluoropyridine(315190-38-6)
• EPA Substance Registry System: 4-(diphenylphosphinyl)-2,3,5,6-tetrafluoropyridine(315190-38-6)

Safety Data

• Hazardous Substances Data: 315190-38-6(Hazardous Substances Data)

Upstream product

• 700-16-3 Pentafluoropyridine 
• 829-85-6 diphenylphosphane 
• 17154-34-6 (trimethylsilyl)diphenylphosphine 

Downstream Products

• 528584-61-4 trans-[RhCl(CO)(PPh₂(C₅F₄N-4))2] 

Relevant articles and documents

Phosphinodefluorination of polyfluorobenzenes by silylphosphines Ph(R)PSiMe3 (R = Me, Ph): Further experimental and computational evidences for the concerted ANDN mechanism of aromatic nucleophilic substitution

Trimethylsilylphosphines PhRPSiMe3 (1 R = Me, 2 R = Ph) have been shown to phosphinodefluorinate 1,2,3- (3), 1,3,5- (4) and 1,2,4-trifluorobenzene (5) in benzene solution or without solvent at 150-200 °C to form the respective (difluorophenyl)methylphenyl- and -diphenylphosphines in high NMR yields under harder conditions compared to the previously reported reactions of Me2PSiMe3 with the same substrates. Hexafluorobenzene (6), pentafluorobenzene (7) (at 150 °C), octafluorotoluene (8) and pentafluoropyridine (9) (at 20 °C) react with phosphine 2 without a solvent almost quantitatively under fluorine 1,4-disubstitution (for 6) or monosubstitution (for 7-9) by the Ph2P group to give the corresponding (polyfluoroaryl)diphenylphosphines in 50-60% (for 6-8) and 95% (for 9) isolated yields. The regio and substrate selectivities exhibited by 3-5 in the reactions of the single substrates and in competitive reactions of 3 vs. 4 with 1 or 2 and 4 vs. 5 with 2 indicate relative fluorine substituent rate factors fo-F > fm-F consistent with the concerted ANDN mechanism which is supported by high level quantum chemical DFT-studies for the reactions of the substrates 3 and 4 with 1, 2 and 10 as well as for 6 with 2.