4,4'-Biphenol

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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
EC Number 202-200-5
KEGG
UNII
Properties
C12H10O2
Molar mass 186.21 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
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

Safety[edit]

Vanadium(IV) chloride is estrogenic[4] and cytotoxic.[5]

References[edit]

  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, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus (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. Encyclopedia of Reagents for Organic Synthesis. New York, NY: J. Wiley & Sons. doi:10.1002/047084289X.rv001.
  4. ^ Kuiper, George G. J. M.; Lemmen, Josephine G.; Carlsson, Bo; Corton, J. Christopher; Safe, Stephen H.; Van Der Saag, Paul T.; Van Der Burg, Bart; Gustafsson, Jan-Ake (1998). "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β". Endocrinology. 139: 4252–4263. doi:10.1210/endo.139.10.6216.
  5. ^ Murakami, Y.; Ishii, H.; Hoshina, S.; Takada, N.; Ueki, A.; Tanaka, S.; Kadoma, Y.; Ito, S.; Machino, M.; Fujisawa, S. (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.