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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
  • 121627-17-6
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9041113
EC Number
  • 700-178-6
  • 329762141
UNII
  • LKX6732VAP Y
  • 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
  • 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
C46H44O8P2
Molar mass 786.798 g·mol−1
Appearance white solid
Hazards
GHS labelling:
Warning
H315, H319, H335, H412
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).

See also

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.

biphephos, organophosphorus, compound, that, used, ligand, homogeneous, catalysis, classified, diphosphite, derived, from, three, biphenol, groups, which, constrain, shape, such, confer, high, selectivity, derived, catalysts, originally, described, workers, un. 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 NamesPreferred 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 IdentifiersCAS Number 121627 17 63D model JSmol Interactive imageChemSpider 9041113EC Number 700 178 6PubChem CID 329762141UNII LKX6732VAP YInChI 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 8H3Key WUFGFUAXCBPGOL UHFFFAOYSA NSMILES 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 OCPropertiesChemical formula C 46H 44O 8P 2Molar mass 786 798 g mol 1Appearance white solidHazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335 H412Precautionary statements P261 P264 P271 P273 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSee also Edit2 2 Biphenylene phosphorochloridite C12H8O2PCl precursor to BiPhePhos References Edit Gual Aitor Godard Cyril de la Fuente Veronica Castillon 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 a 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 Retrieved from https en wikipedia org w index php title BiPhePhos amp oldid 1105305087, wikipedia, wiki, book, books, library,

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