2,2'-Biphenol

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2,2′-Biphenol
2,2'-biphenol.svg
Names
Preferred IUPAC name
[1,1′-Biphenyl]-2,2′-diol
Other names
o,o′-Dihydroxybiphenyl
Identifiers
3D model (JSmol)
1638363
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.730 Edit this at Wikidata
EC Number
  • 217-303-0
51261
KEGG
UNII
  • InChI=1S/C12H10O2/c13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8,13-14H
    Key: IMHDGJOMLMDPJN-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)C2=CC=CC=C2O)O
Properties
C12H10O2
Molar mass 186.210 g·mol−1
Appearance white solid
Melting point 109 °C (228 °F; 382 K)
Boiling point 320 °C (608 °F; 593 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H315, H318, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, 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).

2,2′-Biphenol is an organic compound with the formula (C6H4OH)2. It is one of three symmetrical isomers of biphenol. A white solid, it is a precursor to diphosphite ligands that are used to support industrial hydroformylation catalysis.[1][2]

BiPhePhos is representative diphosphite ligand derived from 2,2′-biphenol.

Synthesis[edit]

Ring-opening of Dibenzofuran affords 2,2′-biphenol. Alternatively, it can be produced from 2,4-di-tert-butylphenol in two steps. The first step entails oxidative coupling to give the 2,2′-biphenol with four tert-Bu substituents. This species then undergoes debutylation.[3]

See also[edit]

References[edit]

  1. ^ 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: 2066–2068. doi:10.1021/ja00058a079.
  2. ^ 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: 835–847. doi:10.1021/OM950549K.
  3. ^ Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.