113088-15-6

Basic information

• Product Name: 1,1,2-tris(diphenylphosphanyl)ethene
• Synonyms: 1,1,2-tris(diphenylphosphanyl)ethene
• CAS NO: 113088-15-6
• Molecular Weight: 580.585
• Mol File: 113088-15-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,1,2-tris(diphenylphosphanyl)ethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2-tris(diphenylphosphanyl)ethene(113088-15-6)
• EPA Substance Registry System: 1,1,2-tris(diphenylphosphanyl)ethene(113088-15-6)

Safety Data

• Hazardous Substances Data: 113088-15-6(Hazardous Substances Data)

Upstream product

• 829-85-6 diphenylphosphane 
• 5112-95-8 bis(diphenylphosphino)acetylene 
• 1079-66-9 chloro-diphenylphosphine 
• 983-81-3 trans-1,2-bis(diphenylphosphino)ethylene 
• 983-80-2 cis-1,2-bis-(diphenylphosphino)ethene 

Downstream Products

• 153477-75-9 1,1,2-tris(diphenylphosphanyl)cyclopropane 
• 120905-06-8 1,1-bis(boranatodiphenylphosphonio)-2-(diphenylphosphino)-ethene 
• 120883-42-3 trans-1,2-Bis(diphenylphosphino)-1-(methyldiphenylphosphino)ethen-iodid 
• 120883-43-4 Tris(diphenylthiophosphinyl)ethen 

Relevant articles and documents

The synthesis, nuclear magnetic resonance spectra, crystal structure and solid-state and solution conformations of tris(diphenylphosphino)ethene (tppee)

The synthesis of tris(diphenylphosphino)ethene (tppee) by addition of Ph2Ph to Ph2PCCPPh2, or by the reaction of Ph2PCl with Ph2PCLi:CHPPh2, and its crystal structure are described.Crystals of tppee are monoclinic, space group C2/c with a 3553.0(4), b 1044.1(1), c 1855.7(2) pm, β 93.40(1) deg, and Z=8; final R=0.0597 for 4585 observed reflections.The proton, 13C and 31P NMR parameters are reported, and the P-P and P-C coupling constants suggest a solution conformation that is close to that found by X-ray diffraction on the solid; that is, a close approach of the electron lone pairs of the cis-vicinal phosphorus atoms, and opposition of those on the geminal phosphorus atoms.

Ambiedentate Poly(diphenylphosphino)ethanes and -ethenes

Base-catalyzed hydrophosphorylation of CH2=C(PPh2)2 (1) using Ph2PH affords 1,1,2-tris(diphenylphosphino)ethane (2) in high yield.This product is converted into the trisulfide 3 when treated with sulfur, and into a monoquaternary salt 4, when treated with MeI.The onium center appears at one of the two geminal phosphine groups.Treatment of 4 with KH in tetrahydrofuran yields the corresponding ylide 5 as an unstable product.Excess MeI reagent causes P-C cleavage in 1 or 4, but only I2 (6) was identified among several products. - Base-catalyzed addition of Ph2PH to Ph2PCCPPh2 affords tris(diphenylphosphino)ethene (7) whose molecular structure has been determined by X-ray crystallography.The conformation is similar to that in the reference compounds 1 and cis-Ph2P-CH=CH-PPh2.Judged from its only minor distortions, the C=C unit in 7 is not severely affected by either steric or electronic effects of the Ph2P groups.The hydrophosphorylation of Ph2PCCPPh2 with Ph2PH yields yellow 1,2,3,4-tetrakis(diphenylphosphino)-1,3-butadiene (8) as a by-product.