4,4'-Biphenol

4,4'-Biphenol
Names
	Preferred IUPAC name [1,1'-Biphenyl]-4,4'-diol
	Other names 4,4'-Dihydroxybiphenyl; 4,4'-Diphenol; 4,4'-Biphenyldiol
Identifiers
CAS Number	92-88-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34367 ;
ChEMBL	ChEMBL76398 ;
ChemSpider	6845 ;
ECHA InfoCard	100.002.001
EC Number	202-200-5;
KEGG	C14297 ;
PubChem CID	7112;
UNII	R8994A0904;
CompTox Dashboard (EPA)	DTXSID1029120 ;
	InChI InChI=1S/C12H10O2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8,13-14H Key: VCCBEIPGXKNHFW-UHFFFAOYSA-N ; InChI=1/C12H10O2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8,13-14H Key: VCCBEIPGXKNHFW-UHFFFAOYAM;
	SMILES Oc2ccc(c1ccc(O)cc1)cc2;
Properties
Chemical formula	C12H10O2
Molar mass	186.210 g·mol−1
Appearance	colorless or white solid
Melting point	283 °C (541 °F; 556 K)[1]
Boiling point	Sublimes
Solubility in water	Insoluble in water; Soluble in ethanol and ether
Hazards
Safety data sheet	MSDS
Flash point	> 93.3 °C (199.9 °F; 366.4 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

4,4'-Biphenol is an organic compound which is a phenolic derivative of biphenyl. It is a colorless solid.

4,4'-Biphenol is prepared by dealkylation of the tetra t-butyl derivative, generated by the oxidative coupling of 2,6-di-tert-butylphenol. The oxidative coupling of phenol itself typically gives a mixture of isomers.[2] For example, VCl₄ reacts with phenols give 4,4'-, 2,4'-, and 2,2'-biphenols:[3]

2 C₆H₅OH + 2 VCl₄ → HOC₆H₄–C₆H₄OH + 2 VCl₃ + 2 HCl

An earlier process using oxygen and copper salts to enable the oxidative coupling was reported [4]

Safety

Vanadium(IV) chloride is estrogenic[5] and cytotoxic.[6]

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References

Chen, Guoliang; Du, Fangyu; Zhou, Qifan; Liu, Dongdong; Fang, Ting; Shi, Yajie; Du, Yang (2018-01-31). "Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis (Supporting Information)". Synlett. 29 (06): 779–784. doi:10.1055/s-0036-1591892. ISSN 0936-5214.
Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; et al. (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
O’Brien, M. K.; Vanasse, B. (2004). "Vanadium(IV) Chloride". In Paquette, L. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York, NY: J. Wiley & Sons. doi:10.1002/047084289X.rv001.
Hay, Allan (1971). "Coupling of Phenols With Diphenoquinones". US Patent 3,631,208. Retrieved 5 March 2020.
Kuiper, George G. J. M.; Lemmen, Josephine G.; Carlsson, Bo; et al. (1998). "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β". Endocrinology. 139: 4252–4263. doi:10.1210/endo.139.10.6216. PMID 9751507.
Murakami, Y.; Ishii, H.; Hoshina, S.; et al. (2009). "Antioxidant and Cyclooxygenase-2-inhibiting Activity of 4,4'-Biphenol, 2,2'-Biphenol and Phenol" (pdf). Anticancer Research. 29 (6): 2403–2410. PMID 19528508.

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[1] Chen, Guoliang; Du, Fangyu; Zhou, Qifan; Liu, Dongdong; Fang, Ting; Shi, Yajie; Du, Yang (2018-01-31). "Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis (Supporting Information)". Synlett. 29 (06): 779–784. doi:10.1055/s-0036-1591892. ISSN 0936-5214.

[Ullmann-2] Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; et al. (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.

[3] O’Brien, M. K.; Vanasse, B. (2004). "Vanadium(IV) Chloride". In Paquette, L. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York, NY: J. Wiley & Sons. doi:10.1002/047084289X.rv001.

[4] Hay, Allan (1971). "Coupling of Phenols With Diphenoquinones". US Patent 3,631,208. Retrieved 5 March 2020.

[5] Kuiper, George G. J. M.; Lemmen, Josephine G.; Carlsson, Bo; et al. (1998). "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β". Endocrinology. 139: 4252–4263. doi:10.1210/endo.139.10.6216. PMID 9751507.

[6] Murakami, Y.; Ishii, H.; Hoshina, S.; et al. (2009). "Antioxidant and Cyclooxygenase-2-inhibiting Activity of 4,4'-Biphenol, 2,2'-Biphenol and Phenol" (pdf). Anticancer Research. 29 (6): 2403–2410. PMID 19528508.