BiPhePhos

BiPhePhos is an organophosphorus compound that is used as a ligand in homogeneous catalysis. Classified as a diphosphite, BiPhePhos is derived from three 2,2'-biphenol groups, which constrain its shape in such a way to confer high selectivity to derived catalysts.^[1] Originally described by workers at Union Carbide,^[2] it has become a standard ligand in hydroformylation.^[3][4]

BiPhePhos

Names
Preferred IUPAC name 6,6′-[(3,3′-Di-tert-butyl-5,5′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(oxy)]bis(6H-dibenzo[d,f][1,3,2]dioxaphosphepine)
Identifiers
CAS Number	121627-17-6
3D model (JSmol)	Interactive image
ChemSpider	9041113
EC Number	700-178-6
PubChem CID	329762141
UNII	LKX6732VAP Y
CompTox Dashboard (EPA)	DTXSID60746295
InChI InChI=1S/C46H44O8P2/c1-45(2,3)37-27-29(47-7)25-35(43(37)53-55-49-39-21-13-9-17-31(39)32-18-10-14-22-40(32)50-55)36-26-30(48-8)28-38(46(4,5)6)44(36)54-56-51-41-23-15-11-19-33(41)34-20-12-16-24-42(34)52-56/h9-28H,1-8H3 Key: WUFGFUAXCBPGOL-UHFFFAOYSA-N
SMILES CC(C)(C)C1=CC(=CC(=C1OP2OC3=CC=CC=C3C4=CC=CC=C4O2)C5=C(C(=CC(=C5)OC)C(C)(C)C)OP6OC7=CC=CC=C7C8=CC=CC=C8O6)OC
Properties
Chemical formula	C46H44O8P2
Molar mass	786.798 g·mol−1
Appearance	white solid
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H412
Precautionary statements	P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• 2,2'-Biphenylene phosphorochloridite (C₁₂H₈O₂PCl) precursor to BiPhePhos.

References

1. Gual, Aitor; Godard, Cyril; de la Fuente, Verónica; Castillón, Sergio (2012). "Design and Synthesis of Phosphite Ligands for Homogeneous Catalysis". Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis. pp. 81–131. doi:10.1002/9781118299715.ch3. ISBN 9781118299715.
2. Billig, Ernst; Abatjoglou, Anthony G.; Bryant, David R. (1988). "Homogeneous Rhodium Carbonyl Compound-Phosphite Ligand Catalysts and Process for Olefin Hydroformylation". US 4769498 a 19880906 to Union Carbide.
3. Cuny, Gregory D.; Buchwald, Stephen L. (1993). "Practical, High-Yield, Regioselective, Rhodium-Catalyzed Hydroformylation of Functionalized α-olefins". Journal of the American Chemical Society. 115 (5): 2066–2068. doi:10.1021/ja00058a079.
4. Van Rooy, Annemiek; Kamer, Paul C. J.; Van Leeuwen, Piet W. N. M.; Goubitz, Kees; Fraanje, Jan; Veldman, Nora; Spek, Anthony L. (1996). "Bulky Diphosphite-Modified Rhodium Catalysts: Hydroformylation and Characterization". Organometallics. 15 (2): 835–847. doi:10.1021/OM950549K.