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]
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Names | |
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IUPAC name
6-[2-(2-benzo[d][1,3,2]benzodioxaphosphepin-6-yloxy-3-tert-butyl-5-methoxyphenyl)-6-tert-butyl-4-methoxyphenoxy]benzo[d][1,3,2]benzodioxaphosphepine | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
EC Number |
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PubChem CID |
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Properties | |
C46H44O18P2 | |
Molar mass | 946.788 g·mol−1 |
Appearance | white solid |
Hazards | |
GHS pictograms | ![]() |
GHS Signal word | Warning |
GHS hazard statements |
H315, H319, H335, H412 |
P261, P264, P271, P273, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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See also
- 2,2'-Biphenylene phosphorochloridite (C12H8O2PCl) precursor to BiPhePhos.
References
- 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.
- 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.
- 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.
- 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.
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