4,4'-Biphenol

4,4′-Biphenol
Displayed structure of a 4,4′-biphenol molecule
Displayed structure of a 4,4′-biphenol molecule
3D model 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

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

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

See also

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 (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.

Read other articles:

Bhulabhai Desai

Jawaharlal Nehru, Bhulabhai Desai dan Babu Rajendra Prasad (tengah) di Sesi AICC, April 1939 Bhulabhai Desai (13 Oktober 1877 – 6 Mei 1946) adalah seorang aktivis kemerdekaan dan pengacara India. Ia dikenal karena membela tiga prajurit Tentara Nasional India yang dituduh melakukan penyiksaan pada masa Perang Dunia II, dan berupaya menegosiasikan perjanjian pembagian kekuasaan rahasia dengan Liaquat Ali Khan dari Liga Muslim. Referensi Rajmohan Gandhi, Patel: A Life (1992) Moti...

 

Armand Van Helden

Armand Van HeldenBiografiKelahiran16 Februari 1970 (54 tahun)Boston Data pribadiPendidikanUniversitas Boston KegiatanSpesialisasiMusik PekerjaanDisjoki, produser rekaman, komponis dan pemusik Periode aktif1990  –GenreGarage house (en) dan musik house Label rekamanNervous Records (en) Situs web<span%20class= penicon%20data-bridge-edit-flow=single-best-value> Laman resmi Armand Van Helden (lahir 16 Februari 1970) adalah seorang dj dan produsen musik bergaya House dari Amerika Serik...

 

Dadapayam, Suruh, Semarang

DadapayamDesaPeta lokasi Desa DadapayamNegara IndonesiaProvinsiJawa TengahKabupatenSemarangKecamatanSuruhKode pos50776Kode Kemendagri33.22.04.2017 Luas8,4687 km²Jumlah penduduk6103 jiwaKepadatan718 jiwa/km² Dadapayam adalah sebuah desa di kecamatan Suruh, Semarang, Jawa Tengah, Indonesia. Desa ini terletak di Kec. Suruh, Kab. Semarang merupakan Desa paling utara dari Kecamatan Suruh sekitar 11 km dari Suruh, tepatnya di 15 km arah timur dari Kota Salatiga, 50 km dari Kota Ungaran dan 6...

1916 New Hampshire gubernatorial election

Election For related races, see 1916 United States gubernatorial elections. 1916 New Hampshire gubernatorial election ← 1914 November 7, 1916 1918 →   Nominee Henry W. Keyes John C. Hutchins Party Republican Democratic Popular vote 45,851 38,853 Percentage 53.20% 45.08% Governor before election Rolland H. Spaulding Republican Elected Governor Henry W. Keyes Republican Elections in New Hampshire Federal government Presidential elections 1788–89 1792 1796 1800 ...

 

1990–91 OHL season

The 1990–91 OHL season was the 11th season of the Ontario Hockey League. Sixteen teams each played 66 games. The Sault Ste. Marie Greyhounds won the J. Ross Robertson Cup, defeating the Oshawa Generals. The Detroit Compuware Ambassadors are granted a franchise. Expansion/Realignment Detroit Compuware Ambassadors On December 11, 1989, the Detroit Compuware Ambassadors were approved to join the league for the 1990–91 season as an expansion team. The club was owned by former Windsor Compuwar...

 

Merah marak

Merah Marak Makaw merahCommon connotationsKeberanian, Hasrat     Koordinat warnaTriplet hex#FF2400sRGBB    (r, g, b)(255, 36, 0)HSV       (h, s, v)(8.5°, 100%, 100%)SumberDaftar Istilah Warna[1]X11B: Dinormalkan ke [0–255] (bita) Merah marak (Inggris: Scarlet) adalah suatu corak warna merah menyala. Warna ini sudah digunakan sejak era Republik Romawi, dimana pejabat tingkat tinggi mengenakan pakaian berwarna ini. Rujukan ^ Adiwimarta,...

energetically modified cement

Class of cements, mechanically processed to transform reactivity An EMC made from volcanic rocks (Luleå, Sweden, 2020) Energetically modified cements (EMCs) are a class of cements made from pozzolans (e.g. fly ash, volcanic ash, pozzolana), silica sand, blast furnace slag, or Portland cement (or blends of these ingredients).[1] The term energetically modified arises by virtue of the mechanochemistry process applied to the raw material, more accurately classified as high energy ball m...

 

Aneka Tambang

Artikel ini terlalu bergantung pada referensi dari sumber primer. Mohon perbaiki artikel ini dengan menambahkan sumber sekunder atau tersier. (Pelajari cara dan kapan saatnya untuk menghapus pesan templat ini) PT Aneka Tambang TbkKantor pusat di JakartaNama dagangANTAMJenisPerusahaan publikKode emitenIDX: ANTMASX: ATMIndustriPertambanganPendahuluPN Tambang Bauksit IndonesiaPN Tambang Emas CikotokPN Logam MuliaDidirikan5 Juli 1968; 55 tahun lalu (1968-07-05)KantorpusatJakarta, Indone...

 

Unione Sportiva Lucchese Libertas 1951-1952

Voce principale: Associazione Sportiva Lucchese Libertas 1905. Unione Sportiva Lucchese LibertasStagione 1951-1952Sport calcio Squadra Lucchese Allenatore Luigi Ferrero, poi dalla 10ª Piero Andreoli Presidente Umberto Paradossi Serie A18º posto (Retrocessa in Serie B) Maggiori presenzeCampionato: De Fazio, Greco (38) Miglior marcatoreCampionato: Frandsen (12) 1950-1951 1952-1953 Si invita a seguire il modello di voce Questa voce raccoglie le informazioni riguardanti il l'Unione Sporti...

Gilgit-Baltistan

Gilgit-Baltistan گلگت - بلتستانUnit AdministrasiGilgit-Baltistān Lambang resmi Gilgit-BaltistanLambangLokasi Gilgit-Baltistan (merah)Negara PakistanDidirikan1 Juli 1970IbukotaGilgitKota besarGilgitPemerintahan • JenisOtonomi • GubernurPir Karam Ali Shah[1] • Perdana MenteriSyed Mehdi Shah[2]Luas • Total72.971 km2 (28,174 sq mi)Populasi (2008; angg.) • Total1.800.000 • K...

 

Salemi

Disambiguazione – Se stai cercando altri significati, vedi Salemi (disambigua). Salemicomune Salemi – Veduta LocalizzazioneStato Italia Regione Sicilia Libero consorzio comunale Trapani AmministrazioneSindacoDomenico Venuti (lista civica) dal 28-5-2014 (2º mandato dal 30-4-2019) TerritorioCoordinate37°49′N 12°48′E / 37.816667°N 12.8°E37.816667; 12.8Coordinate: 37°49′N 12°48′E / 37.816667°N 12.8°E37.816667; ...

 

Italian city-states

Political entities in medieval Italy Part of a series on the History of Italy Early Prehistoric Italy Nuragic civilization (18th–3rd c. BC) Etruscan civilization (12th–6th c. BC) Magna Graecia (8th–3rd c. BC) Ancient Rome Kingdom (753 BC–509 BC) Republic (509 BC–27 BC) Roman expansion in Italy Roman Italy Populares and Optimates Empire (27 BC–286 AD) Western Empire (286 AD–476 AD) Praetorian prefecture of Italy Romano-Barbarian Kingdoms Odoacer's 476&...

1923 Philadelphia mayoral election

Philadelphia mayoral election 1923 Philadelphia mayoral election← 19191927 →   Nominee W. Freeland Kendrick A. Raymond Raff Party Republican Democratic Popular vote 286,398 37,239 Percentage 88.49% 11.51% Mayor before election J. Hampton Moore Republican Elected Mayor W. Freeland Kendrick Republican Elections in Pennsylvania Federal government U.S. President 1789 1792 1796 1800 1804 1808 1812 1816 1820 1824 1828 1832 1836 1840 1844 1848 1852 1856 1860 1864 1868...

 

Rasmus Kristensen

Rasmus Kristensen Nazionalità  Danimarca Altezza 186 cm Peso 70 kg Calcio Ruolo Difensore Squadra  Roma CarrieraGiovanili 2003-2010 Brande IF2010-2012 Herning Fremad2012-2016 MidtjyllandSquadre di club1 2016-2018 Midtjylland54 (5)[1]2018-2019 Ajax20 (0)2019-2022 Salisburgo72 (10)2022-2023 Leeds Utd26 (3)2023-→  Roma26 (1)Nazionale 2015 Danimarca U-185 (1)2015-2016 Danimarca U-1913 (2)2016 Danimarca U-201 (0)2016-2019 Danimarca U-2127 (6...

 

Голубянки

Голубянки Самец голубянки икар Научная классификация Домен:ЭукариотыЦарство:ЖивотныеПодцарство:ЭуметазоиБез ранга:Двусторонне-симметричныеБез ранга:ПервичноротыеБез ранга:ЛиняющиеБез ранга:PanarthropodaТип:ЧленистоногиеПодтип:ТрахейнодышащиеНадкласс:ШестиногиеКласс...

Joan Russow

Canadian peace activist For other uses, see Russow. This biography of a living person needs additional citations for verification. Please help by adding reliable sources. Contentious material about living persons that is unsourced or poorly sourced must be removed immediately from the article and its talk page, especially if potentially libelous.Find sources: Joan Russow – news · newspapers · books · scholar · JSTOR (September 2016) (Learn how and when...

 

Muscolo popliteo

Le informazioni riportate non sono consigli medici e potrebbero non essere accurate. I contenuti hanno solo fine illustrativo e non sostituiscono il parere medico: leggi le avvertenze. Muscolo popliteoSi osserva il muscolo popliteoAnatomia del Gray(EN) Pagina 484 SistemaSistema muscolare OrigineSolco popliteo InserzioneSuperficie posteriore della tibia AzioniInteressa la flessione della gamba sulla coscia e al contrario. NervoInnervato dal tibiale IdentificatoriTAA04.7.02.050 FMA22590 Modifi...

 

Northwest Hills Planning Region, Connecticut

Northwest Hills redirects here. For the informal geographic region of Connecticut, see Litchfield Hills. Planning region in ConnecticutNorthwest Hills Planning RegionPlanning regionNorthwest Hills Council of Governments (NHCOG)From top left: Naugatuck River in Torrington, Mohawk Mountain Ski Area, Kent Falls State Park, Main Street in North Canaan, West Street in Litchfield LogoLocation within the U.S. state of ConnecticutConnecticut's location within the U.S.Coordinates: 41°50′N 73°13′...

Coupe de la Major League Soccer 2007

Cet article est une ébauche concernant une compétition de football. Vous pouvez partager vos connaissances en l’améliorant (comment ?) selon les recommandations des projets correspondants. Coupe de la Major League Soccer 2007 Généralités Sport Football Organisateur(s) Major League Soccer Lieu(x) Stade Robert F. Kennedy Washington DC Date 18 novembre 2007 Participants Revolution de la Nouvelle-AngleterreDynamo de Houston Palmarès Vainqueur Dynamo de Houston Navigation Édition p...

 

AIM-4 Falcon

Hughes AIM-4 Falcon adalah sebuah peluru kendali / rudal udara-ke-udara dipandu yang pertama operasional dari Angkatan Udara Amerika Serikat. Pembangunan dimulai pada tahun 1946, senjata pertama kali diuji pada tahun 1949. Rudal itu memasuki layanan dengan USAF pada tahun 1956. Referensi The history of the Falcon missile, and its various configurations, is examined in Gart, Jason H. Electronics and Aerospace Industry in Cold War Arizona, 1945-1968: Motorola, Hughes Aircraft, Goodyear Aircraf...