Chemistry:4,4'-Biphenol
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| Names | |
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| Preferred IUPAC name
[1,1′-Biphenyl]-4,4′-diol | |
| Other names
4,4′-Dihydroxybiphenyl
4,4′-Diphenol 4,4′-Biphenyldiol | |
| Identifiers | |
3D model (JSmol)
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| 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 | |
| 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 | |
Tracking categories (test):
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
4,4'-Biphenol had actually been elucidated to have an estrogenic SAR.[5]
See also
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)" (in en). Synlett 29 (6): 779–784. doi:10.1055/s-0036-1591892. ISSN 0936-5214. https://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591892.
- ↑ Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch et al. (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.
- ↑ 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. ISBN 0471936235.
- ↑ Hay, Allan (1971). "Coupling of Phenols With Diphenoquinones". https://pdfpiw.uspto.gov/.piw?docid=03631208&PageNum=1&&IDKey=4683FDD170D1&HomeUrl=http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1%2526Sect2=HITOFF%2526p=1%2526u=%25252Fnetahtml%25252FPTO%25252Fsearch-bool.html%2526r=1%2526f=G%2526l=50%2526d=PALL%2526S1=3631208.PN.%2526OS=PN/3631208%2526RS=PN/3631208.
- ↑ 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.
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