851869-38-0

Basic information

• Product Name: Diphenyl-[4-(1H,1H,2H,2H-perfluorodecyl)phenyl]phosphine oxide
• CAS NO: 851869-38-0
• Molecular Weight: 724.397
• Mol File: 851869-38-0.mol

Chemical Properties

• CAS DataBase Reference: Diphenyl-[4-(1H,1H,2H,2H-perfluorodecyl)phenyl]phosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenyl-[4-(1H,1H,2H,2H-perfluorodecyl)phenyl]phosphine oxide(851869-38-0)
• EPA Substance Registry System: Diphenyl-[4-(1H,1H,2H,2H-perfluorodecyl)phenyl]phosphine oxide(851869-38-0)

Safety Data

• Hazardous Substances Data: 851869-38-0(Hazardous Substances Data)

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 195324-88-0 1-(4'-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane 
• 6427-66-3 4-azidobenzoic acid 
• 462996-04-9 bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine 

Downstream Products

• 462996-04-9 bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine 

Relevant articles and documents

Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines

(Equation Presented) The relative reactivities of triphenylphosphine (PPh3) and three fluorous triarylphosphines [(p-RF(CH 2)2C6H4)nPPh 3-n, where n = 1-3] have been compared in internal competition experiments. Product ratios were determined by 31P NMR spectroscopy. The four phosphines have about the same reactivities in oxidation, alkylation, and Staudinger reactions and give comparable yields in a preparative Mitsunobu reaction. Previously observed rate and yield differences in Staudinger reactions of the fluorous phosphines are attributed to solubility effects, not reactivity differences. A light fluorous phosphine [(p-C8F17(CH 2)2C6H4PPh2] outperforms a commercially available resin-bound phosphine in a competitive benzylation experiment by a factor of about 4.

Fluorous Mitsunobu reagents and reactions

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse.