(1,1'-Biphenyl)-4,4'-diol

4,4′-Biphenol
Displayed structure of a 4,4′-biphenol molecule
3D model of a 4,4′-biphenol molecule
Names
Preferred IUPAC name
[1,1′-Biphenyl]-4,4′-diol
Other names
4,4′-Dihydroxybiphenyl
4,4′-Diphenol
4,4′-Biphenyldiol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.001 Edit this at Wikidata
EC Number
  • 202-200-5
KEGG
UNII
  • InChI=1S/C12H10O2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8,13-14H checkY
    Key: VCCBEIPGXKNHFW-UHFFFAOYSA-N checkY
  • 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
  • Oc2ccc(c1ccc(O)cc1)cc2
Properties
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
Insoluble in water
Soluble in ethanol and ether
Hazards
Flash point > 93.3 °C (199.9 °F; 366.4 K)
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

4,4'-Biphenol had actually been elucidated to have an œstrogenic SAR.[7]

References[]

  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.
  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.
  7. ^ Dodds, E. C.; Lawson, W. (1937). "A Simple Aromatic (strogenic Agent with an Activity of the Same Order as that of strone". Nature. 139 (3519): 627–628. doi:10.1038/139627b0. ISSN 0028-0836.