2,2'-Biphenol

2,2′-Biphenol
Names
	Preferred IUPAC name [1,1′-Biphenyl]-2,2′-diol
	Other names o,o′-Dihydroxybiphenyl
Identifiers
CAS Number	1806-29-7;
3D model (JSmol)	Interactive image;
Beilstein Reference	1638363
ChEBI	CHEBI:28970;
ChEMBL	ChEMBL183874;
ChemSpider	14959;
ECHA InfoCard	100.015.730
EC Number	217-303-0;
Gmelin Reference	51261
KEGG	C03209;
PubChem CID	15731;
UNII	PM2R53I3C9;
CompTox Dashboard (EPA)	DTXSID6051809 ;
	InChI 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;
	SMILES C1=CC=C(C(=C1)C2=CC=CC=C2O)O;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H318, H319, H335
Precautionary statements	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). Infobox references

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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

The chemical can be made by a hydrolysis reaction that opens the central ring of dibenzofuran. 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-butyl substituents. This species then undergoes debutylation.^[3]

References

^ 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.
^ Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D.; Paulus, W. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.

[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 (5): 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 (2): 835–847. doi:10.1021/OM950549K.

[Ullmann-3] Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D.; Paulus, W. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.

[1]

[2]

[3]

Synthesis

See also

References