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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 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).
checkY verify (what is checkY☒N ?)

4,4′-Biphenol is an aromatic organic compound, and one of three symmetrical isomers of biphenol. It is a colourless crystalline solid with a high melting point. It is primarily used in the production of polymers, particularly liquid crystals where it imparts high thermal stability.

Synthesis

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The industrial synthesis of 4,4′-biphenol was developed by Allan Hay in the 1960s.[2][3] As the direct oxidative coupling of phenol gives a mixture of isomers,[4][5] 4,4′-biphenol is instead prepared from 2,6-di-tert-butylphenol, where para-coupling is the only possibility.[3] The reaction with oxygen produces phenol-radicals which undergo rapid dimerisation, forming a diphenoquinone. This is reduced to the tetra-butyl-biphenyl derivative by a reaction with additional 2,6-di-tert-butylphenol, in an oxygen-free environment.[2] In the final step, high temperature dealkylation is performed to remove the butyl groups, producing the desired 4,4′-biphenol product.[3] If groups less bulky that t-butyl are used then polyphenylene ethers such as poly(p-phenylene oxide) can be produced.[6]

Safety

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

See also

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References

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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 (6): 779–784. doi:10.1055/s-0036-1591892. ISSN 0936-5214. S2CID 104289422.
  2. ^ a b Hay, A.S. (January 1965). "Dehydrogenation reactions with diphenoquinones". Tetrahedron Letters. 6 (47): 4241–4243. doi:10.1016/S0040-4039(01)89114-0.
  3. ^ a b c Hay, Allan S. (April 1969). "p,p'-Biphenols". The Journal of Organic Chemistry. 34 (4): 1160–1161. doi:10.1021/jo01256a098.
  4. ^ 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. ISBN 3527306730.
  5. ^ 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. ISBN 0471936235.
  6. ^ Hay, Allan S. (April 1962). "Polymerization by oxidative coupling. II. Oxidation of 2,6‐disubstituted phenols". Journal of Polymer Science. 58 (166): 581–591. doi:10.1002/pol.1962.1205816634.
  7. ^ Dodds, E. C.; Lawson, W. (1937). "A Simple Aromatic oestrogenic Agent with an Activity of the Same Order as that of estrone". Nature. 139 (3519): 627–628. doi:10.1038/139627b0. ISSN 0028-0836. S2CID 4119670.