Production Method 1

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium ,  Lignin Solvents: Water ;  0.5 h, 70 °C

Reference

Palladium nanoparticles, stabilized by lignin, as catalyst for cross-coupling reactions in water

Coccia, Francesca; Tonucci, Lucia; d'Alessandro, Nicola; D'Ambrosio, Primiano; Bressan, Mario, Inorganica Chimica Acta, 2013, 399, 12-18

Production Method 2

5122-94-1

92-69-3

Reaction Conditions

1.1 Reagents: Triethylamine ,  Oxygen Catalysts: Tetra-μ3-hydroxytetra-μ3-oxotris[μ-[4-[10,15,20-tris(4-carboxyphenyl)-21H,23H-po… Solvents: Acetonitrile ,  Water ;  24 h, pH 7, rt

Reference

Visible-light, photoredox catalyzed, oxidative hydroxylation of arylboronic acids using a metal-organic framework containing tetrakis(carboxyphenyl)porphyrin groups

Toyao, Takashi; Ueno, Nana; Miyahara, Kenta; Matsui, Yasunori; Kim, Tae-Ho; et al, Chemical Communications (Cambridge, 2015, 51(89), 16103-16106

Production Method 3

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium ,  Cellulose Solvents: Water ;  30 min, 100 °C

Reference

Palladium Nanoparticle-Loaded Cellulose Paper: A Highly Efficient, Robust, and Recyclable Self-Assembled Composite Catalytic System

Zheng, Guangchao; Kaefer, Katharina; Mourdikoudis, Stefanos; Polavarapu, Lakshminarayana; Vaz, Belen; et al, Journal of Physical Chemistry Letters, 2015, 6(2), 230-238

Production Method 4

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: 1604839-72-6 (silica-coated iron oxide-bound) Solvents: Water ;  12 h, rt → 80 °C

Reference

A highly water-dispersible/magnetically separable palladium catalyst based on a Fe3O4@SiO2 anchored TEG-imidazolium ionic liquid for the Suzuki-Miyaura coupling reaction in water

Karimi, Babak; Mansouri, Fariborz; Vali, Hojatollah, Green Chemistry, 2014, 16(5), 2587-2596

Production Method 5

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: 1,4-Benzenediamine, polymer with 1,3,5-triisocyanatobenzene (palladium complexes) Solvents: Water ;  3 h, 60 °C

Reference

Urea-Based Porous Organic Frameworks: Effective Supports for Catalysis in Neat Water

Li, Liuyi; Chen, Zhilin; Zhong, Hong; Wang, Ruihu, Chemistry - A European Journal, 2014, 20(11), 3050-3060

Production Method 6

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Water ;  1 h, 70 °C

Reference

Pd nanoparticles immobilized on PNIPAM-halloysite: highly active and reusable catalyst for Suzuki-Miyaura coupling reactions in water

Hong, Myeng Chan; Ahn, Hyunseok; Choi, Myung Chan; Lee, Yongwoo; Kim, Jongsik; et al, Applied Organometallic Chemistry, 2014, 28(3), 156-161

Production Method 7

129236-45-9

92-69-3

Reaction Conditions

1.1 Catalysts: Methanesulfonic acid phenyl ester sulfatase Solvents: Water ;  20 min, pH 7.4, 25 °C

Reference

Simple methanesulfonates are hydrolyzed by the sulfatase carbonic anhydrase activity

Kazancioglu, Elif Akin; Gueney, Murat; Sentuerk, Murat; Supuran, Claudiu T., Journal of Enzyme Inhibition and Medicinal Chemistry, 2012, 27(6), 880-885

Production Method 8

92-69-3

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: 2-Pyridinecarboxaldehyde (reaction products with amino-functionalized divinylbenzene-glycidyl methacrylate-styrene copolymer, palladium complex) ,  Palladium diacetate Solvents: Isopropanol ,  Water ;  0.33 h, 70 °C

Reference

Synthesis of gel-type imino-amino functionalized methacrylate-styrene terpolymers as supports for palladium catalysts for the Suzuki-Miyaura reaction

Bester, Karol; Bukowska, Agnieszka; Bukowski, Wiktor, Applied Catalysis, 2012, 443, 443-444

Production Method 9

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: (SP-4-2)-[1,1′-Bis[bis(1,1-dimethylethyl)phosphino-κP]ferrocene]dichloropalladiu… Solvents: Acetonitrile ,  Water ;  1 - 2 h, 60 °C

Reference

A mild robust generic protocol for the Suzuki reaction using an air stable catalyst

Moseley, Jonathan D.; Murray, Paul M.; Turp, Edward R.; Tyler, Simon N. G.; Burn, Ross T., Tetrahedron, 2012, 68(30), 6010-6017

Production Method 10

5122-94-1

92-69-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: 2,5-Pyridinedicarboxylic acid ,  Diisopropylethylamine ,  Nitric acid, indium(3+) salt, hydrate (3:1:4) Solvents: Ethanol ;  10 h, rt

Reference

Double Insurance of Continuous Band Structure and N-C Layer Induced Prolonging of Carrier Lifetime to Enhance the Long-Wavelength Visible-Light Catalytic Activity of N-Doped In2O3

Sun, Liming; He, Xiaoxiao; Zeng, Suyuan ; Yuan, Yusheng; Li, Rong; et al, Inorganic Chemistry, 2021, 60(2), 1160-1171

Production Method 11

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Tetrabutylammonium bromide ,  Oxygen Catalysts: Palladium ,  1,4-Benzenediamine, polymer with 1,4-diisocyanatobenzene Solvents: Water ;  1 h, 60 °C

Reference

Evaluation of Nitrogen-Based Polymeric Heterogeneous Catalysts for the Suzuki-Miyaura Cross-Coupling Reaction in Water

So, Jae Il ; Hwang, Sosan; Lee, Myeong Yeon; Song, Mingyu; Baeck, Sung-Hyeon ; et al, ACS Applied Polymer Materials, 2020, 2(8), 3122-3134

Production Method 12

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium diacetate (complex with bipyridyl amide bound on silica) Solvents: Water ;  1 h, 80 °C

Reference

Organic chemical reaction catalyst supported palladium on reversed phase silica gel support for forming bi-aryl compound

, Korea, , ,

Production Method 13

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium diacetate ,  1,4-Benzenedicarboxaldehyde, polymer with 4,4′,4′′,4′′′-methanetetrayltetrakis[b… Solvents: Methanol ,  Water ;  20 min, 70 °C

Reference

Heterogeneous Catalysis by Covalent Organic Frameworks (COF): Pd(OAc)2@COF-300 in Cross-Coupling Reactions

Goncalves, Raoni S. B.; de Oliveira, Alline B. V.; Sindra, Haryadylla C.; Archanjo, Braulio S.; Mendoza, Martin E.; et al, ChemCatChem, 2016, 8(4), 743-750

Production Method 14

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Palladium chloride Solvents: Isopropanol ,  Water ;  6 h, 80 °C

Reference

Palladium supported on aminopropyl-functionalized polymethylsiloxane microspheres: Simple and effective catalyst for the Suzuki-Miyaura C-C coupling

Zawartka, Wojciech; Pospiech, Piotr; Cypryk, Marek; Trzeciak, Anna M., Journal of Molecular Catalysis A: Chemical, 2015, 407, 230-235

Production Method 15

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Methanol ;  5 min, 150 psi, 75 °C

Reference

Enhanced heterogeneously catalyzed Suzuki-Miyaura reaction over SiliaCat Pd(0)

Pandarus, Valerica; Desplantier-Giscard, Delphine; Gingras, Genevieve; Ciriminna, Rosaria; Demma Cara, Piera; et al, Tetrahedron Letters, 2013, 54(35), 4712-4716

Production Method 16

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium (silica-supported) Solvents: Ethanol ;  2 h, 77 °C

Reference

Efficient Screening and Library Generation in Parallel C-C Coupling Reactions Mediated by Organosilica SiliaCat Palladium Catalysts

Pandarus, Valerica; Gingras, Genevieve; Beland, Francois; Ciriminna, Rosaria; Pagliaro, Mario, Organic Process Research & Development, 2012, 16(1), 117-122

Production Method 17

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium ,  SiliaCat Pd Solvents: Ethanol ;  2 h, reflux

Reference

A new class of heterogeneous Pd catalysts for synthetic organic chemistry

Pagliaro, Mario; Pandarus, Valerica; Beland, Francois; Ciriminna, Rosaria; Palmisano, Giovanni; et al, Catalysis Science & Technology, 2011, 1(5), 60-63

Production Method 18

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Palladium (complexes with triethoxysilylpropyl-methylimidazolium chloride and acetate) ,  1-Methyl-3-[3-(triethoxysilyl)propyl]imidazolium chloride (palladium acetate complexes) Solvents: Dimethylformamide ,  Water ;  25 min, 70 °C

Reference

Mesoporous MCM-41 supported N-heterocyclic carbene-Pd(II) complex for Suzuki coupling reaction

Alam, Nazmul Md.; Sarkar, Shaheen M., Reaction Kinetics, 2011, 103(2), 493-500

Production Method 19

1124-19-2

92-69-3

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Palladium Solvents: Water ;  24 h, 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Exploring bio-inspired strategies for the production of noble metal nanocatalysts

Knecht, Marc R.; Pacardo, Dennis B.; Coppage, Ryan; Naik, Rajesh R., Polymer Preprints (American Chemical Society, 2010, 51(1), 12-13

Production Method 20

98-80-6

92-69-3

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: (SP-4-3)-[2,6-Bis[(di-1-piperidinylphosphino-κP)amino]phenyl-κC]chloropalladium Solvents: 1-Butanol ,  1,4-Dioxane ,  Water ;  25 °C; 1 h, 25 °C → 100 °C
1.2 Reagents: Water ;  100 °C; 100 °C → rt

Reference

The 1,3-Diaminobenzene-Derived Aminophosphine Palladium Pincer Complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A Highly Active Suzuki-Miyaura Catalyst with Excellent Functional Group Tolerance

Bolliger, Jeanne L.; Frech, Christian M., Advanced Synthesis & Catalysis, 2010, 352(6), 1075-1080

4-Hydroxybiphenyl Raw materials

• Phenylboronic acid
• [1,1'-Biphenyl]-4-ylboronic acid
• Phenyltin trichloride

4-Hydroxybiphenyl Preparation Products

• 4-Hydroxybiphenyl (92-69-3)

• 1. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 2. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 3. Distinct impact of glycation towards the aggregation and toxicity of murine and human amyloid-β?
  Eunju Nam,Jiyeon Han,Sunhee Choi,Mi Hee Lim Chem. Commun., 2021,57, 7637-7640
• 4. Excellent kinetics of single-phase Gd-doped ceria fuel electrodes in solid oxide cells?
  Andreas Nenning,Manuel Holzmann,Jürgen Fleig,Alexander K. Opitz Mater. Adv., 2021,2, 5422-5431
• 5. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives
• Pesticide Chemicals Pesticide Active Ingredients Standard Substances
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

4-Hydroxybiphenyl (CAS No. 92-69-3): A Comprehensive Overview of Its Chemical Properties, Applications, and Recent Research Developments

4-Hydroxybiphenyl, with the chemical formula C₁₂H₁₀O, is a significant organic compound characterized by its biphenyl core structure substituted with a hydroxyl group. This compound, identified by its unique CAS No. 92-69-3, has garnered considerable attention in the scientific community due to its versatile applications and emerging roles in pharmaceuticals, agrochemicals, and material science. The molecular structure of 4-Hydroxybiphenyl imparts distinct chemical properties that make it a valuable intermediate in synthetic chemistry, particularly in the development of more complex molecules.

The biphenyl framework of 4-Hydroxybiphenyl contributes to its stability and reactivity, enabling its use as a precursor in various chemical transformations. One of the most notable aspects of this compound is its role as a building block in the synthesis of more complex organic molecules. Its hydroxyl group allows for further functionalization through esterification, etherification, or oxidation reactions, making it a versatile intermediate in organic synthesis.

In recent years, 4-Hydroxybiphenyl has been extensively studied for its potential applications in pharmaceuticals. Research has demonstrated its utility as a precursor in the synthesis of various bioactive compounds. For instance, derivatives of 4-Hydroxybiphenyl have been investigated for their antimicrobial and anti-inflammatory properties. These studies have highlighted the compound's potential as a lead molecule in drug discovery efforts aimed at developing novel therapeutic agents.

The agrochemical industry has also recognized the significance of 4-Hydroxybiphenyl. Its incorporation into pesticide formulations has shown promise in enhancing the efficacy of these products while maintaining environmental safety. The stability and solubility characteristics of 4-Hydroxybiphenyl make it an ideal candidate for use in crop protection chemicals, contributing to sustainable agricultural practices.

Beyond pharmaceuticals and agrochemicals, 4-Hydroxybiphenyl finds applications in material science. Its molecular structure allows for the development of advanced materials with tailored properties. For example, polymers derived from 4-Hydroxybiphenyl have been explored for their potential use in electronic devices due to their excellent thermal stability and electrical conductivity.

The latest research on 4-Hydroxybiphenyl has revealed new insights into its biochemical interactions and potential therapeutic applications. Studies have shown that certain derivatives of this compound can modulate enzyme activity and cellular pathways involved in diseases such as cancer and neurodegenerative disorders. These findings underscore the importance of continued research into the pharmacological properties of 4-Hydroxybiphenyl.

In conclusion, 4-Hydroxybiphenyl (CAS No. 92-69-3) is a multifaceted compound with broad applications across multiple industries. Its unique chemical properties make it a valuable intermediate in organic synthesis, while its potential therapeutic applications continue to be explored in pharmaceutical research. As advancements are made in understanding the biochemical interactions of this compound, its role in developing innovative solutions for health, agriculture, and technology is expected to grow.

• 92-88-6(4,4'-Dihydroxybiphenyl)
• 4084-45-1([1,1':4',1''-Terphenyl]-4,4''-diol)
• 28826-57-5([1,1'-Biphenyl]-4-ol,homopolymer)
• 15797-52-1(1,3,5-Tri(4-hydroxyphenyl)benzene)
• 1322-21-0(p-Phenylphenol sodium)
• 124526-56-3([1,1':3',1''-Terphenyl]-4,4''-diol)
• 26191-64-0(4-(4-Methylphenyl)phenol)
• 1322-20-9([1,1'-Biphenyl]ol)
• 26983-52-8([1,1'-Biphenyl]-ar,ar'-diol)
• 126840-28-6(4-Hydroxybiphenyl-d9 (rings-d9))