16881-71-3

Basic information

• Product Name: 4-HYDROXY-4'-METHOXYBIPHENYL
• Synonyms: AKOS BAR-1047;4-HYDROXY-4'-METHOXYBIPHENYL;4-HYDROXY-4'-METHOXYDIPHENYL;4'-METHOXY[1,1'-BIPHENYL]-4-OL;4'-METHOXYBIPHENYL-4-OL;Hydroxymethoxybiphenyl;4-HYDROXY-4''-METHOXYBIPHENYL 95+%;4-Hydroxy-4'-methoxybiphenyl
• CAS NO: 16881-71-3
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23
• Product Categories: Biphenyl & Diphenyl ether;Biphenyls (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 16881-71-3.mol

Chemical Properties

• Melting Point: 181°C
• Boiling Point: 344.566 °C at 760 mmHg
• Flash Point: 195.285 °C
• Appearance: /
• Density: 1.13 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: 4-HYDROXY-4'-METHOXYBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-4'-METHOXYBIPHENYL(16881-71-3)
• EPA Substance Registry System: 4-HYDROXY-4'-METHOXYBIPHENYL(16881-71-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 16881-71-3(Hazardous Substances Data)

Usage

Uses

Used in Plastics and Epoxy Resin Manufacturing:
4-Hydroxy-4'-methoxybiphenyl is used as a key component in the production of various plastics and epoxy resins, serving as a substitute for bisphenol A (BPA) to address health concerns associated with BPA. Its application in this industry is driven by the need for alternative materials that maintain the desired properties of plastics while minimizing potential health risks.
Used in Polycarbonate Production:
In the polycarbonate industry, 4-Hydroxy-4'-methoxybiphenyl is utilized as a building block for creating polycarbonate materials, which are known for their strength, transparency, and resistance to heat. The use of BPF in this context aims to provide a safer alternative to BPA-based polycarbonates, catering to the demand for materials with reduced health hazards.
Used in Consumer Product Manufacturing:
4-Hydroxy-4'-methoxybiphenyl is employed in the manufacturing of consumer products such as food and beverage containers, where it replaces BPA to mitigate potential health risks. However, concerns have been raised about BPF's ability to leach from these products, potentially leading to human exposure and health impacts. As a result, the use of BPF in consumer products is subject to ongoing scrutiny and research to ensure safety and compliance with health regulations.

Upstream product

• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 100-66-3 methoxybenzene 
• 106-48-9 4-chloro-phenol 
• 114412-46-3 4-acetoxy-4'-methoxy-1,1'-biphenyl 
• 623-12-1 4-chloromethoxybenzene 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 
• 150-76-5 4-methoxy-phenol 
• 65109-75-3 N-(phenoxy)-4-methylbenzenesulfonamide 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 67019-51-6 1-(4-methoxyphenyl)-1-hydroxycyclohexan-4-one ethylene ketal 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 92-88-6 4,4'-Dihydroxybiphenyl 
• 74-88-4 methyl iodide 

Downstream Products

• 5309-16-0 4-(4-methoxyphenyl)cyclohexanone 
• 173025-52-0 4-[6-(4-methoxybiphenyl-4'-oxy)hexyloxy]-1,3-diaminobenzene 
• 1356963-88-6 C₁₈H₁₄O₃ 
• 1356963-90-0 C₂₀H₁₈O₃ 
• 613-37-6 4-methoxylbiphenyl 
• 6842-78-0 4-butoxy-1,1’-biphenyl 
• 92-52-4 biphenyl 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5123-05-7 2-([1,1'-biphenyl]-4-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 37810-35-8 trans-4-(4-methoxyphenyl)cyclohexanol 
• 60901-08-8 cis-4-(4-Methoxy-phenyl)-cyclohexanol 
• 446311-34-8 2-(4'-methoxy-[1,1^,-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 106869-53-8 6-(4'-methoxybiphenyl-4-oxy)hexanol 

Relevant articles and documents

Pd/C as a reusable catalyst for the coupling reaction of halophenols and arylboronic acids in aqueous media

Pd/C was found to catalyze the Suzuki-Miyaura coupling reaction of halophenols in aqueous media. When halophenols were treated with ArB(OH)2 and a catalytic amount of 10% Pd/C (0.3 mol % Pd) in aqueous K2CO3 solution, the corresponding hydroxybiaryls were obtained in a high yield or quantitatively. The palladium catalyst was easily recovered and reused.

Efficient Syntheses of Star-Branched, Multifunctional Mesogens

Star-branched molecular architectures lend themselves to convergent synthesis strategies for creating materials that combine three or more functional modalities, but these approaches require a core moiety with several reactive groups that are orthogonal t

Novel photochromism of differently-linked bis-benzopyrans

The unique photochromic bis-chromene 5 incorporates the structural attributes of both 3 and 4. UV-vis irradiation of 5 leads to a dark brown colour, which is formed by mixing the purple and red colours observed for the photolysates of 3 and 4, respectively. The Royal Society of Chemistry.

Palladium supported on natural phosphate: Catalyst for Suzuki coupling reactions in water

The Suzuki-Miyaura coupling reaction is one of the most important synthetic catalytic reactions developed in the 20th century. However, the use of toxic organic solvents for this reaction still poses a scientific challenge and is an aspect of economical and ecological relevance. The use of water as a reaction medium overcomes this issue. In the present work, we described efficient Suzuki coupling reactions in water, without any phase transfer reagents and it is possible to couple challenging substrates like aryl chlorides. Notably, this protocol also works with ultra-low loading of catalyst with high turnover numbers.

Microwave assisted cross-coupling reactions using palladium nanoparticles in aqueous media

Glucose stabilized palladium nanoparticles (PdNPs) have been prepared and the application of NPs in catalyzing both Suzuki and Heck reactions has been explored in aqueous media under microwave conditions. Both electron-rich and electron-deficient aryl halides can be coupled with a variety of boronic acids and styrene to access a wide variety of biaryl compounds and substituted alkenes in good to excellent yields. The catalyst can be recycled and reused four times with minimally affecting the morphology and efficiency of the nanoparticles. A plausible reaction mechanism has been proposed.

Counteranion-Controlled Ag2O-Mediated Benzimidazolium Ring Opening and Its Application in the Synthesis of Palladium Pincer-Type Complexes

We report a new approach to synthesize palladium complexes through Ag2O-promoted hydrolytic ring opening followed by palladium coordination. The novelty of Ag2O-promoted hydrolysis in comparison with the commonly used base-mediated hydrolysis lies in the anion-controlled product selectivity in the synthesis of pincer-type palladium complexes. Moreover, these palladium complexes have been tested in the Suzuki reaction using aryl bromides in methanol and H2O, respectively. In comparison with palladium complexes with normal coordination, the palladium complexes generated from the hydrolytic ring-opening coordination demonstrate excellent catalytic activity.

A mixed cyclodextrin-biphenyl thermotropic liquid crystal: Synthesis, liquid-crystalline properties, and supramolecular organization

A well-defined structure liquid crystal heptakis [6deoxy-6-(1-H-1,2,3- triazol-4-yl)(methyl)6-(4-methoxybiphenyl4'-yloxy) hexanoyl]-β-cyclodextrin (H6B-β-CD) was synthesized from propargyl 6-(4-methoxybiphenyl-4′- yloxy) hexanoate (P6B) and heptakis (6-deoxy-6-azido)-β-cyclodextrin ((N3)7-β-CD) by click reaction. The chemical structure of H6B-β-CD was confirmed by 1H NMR, FTIR, and MALDI-TOF MS. The thermal stability of the compound was investigated by thermogravimetric analysis (TGA). The liquid crystalline behavior was studied by differential scanning calorimetry (DSC), polarizing optical microcopy (POM), and wide-angle X-ray diffraction (WAXD) measurement. These investigations have shown that the supramolecular structure of H6B-β-CD are consisted of a large scale ordered lamellar structure and a small scale ordered structure (SmE) at low temperature region. As the temperature increases, the small scale structure becomes disordered relatively in the first instance, from smectic E to smectic A. Then, the lamellar structure collapses and nematic phase and isotropic phase are observed in sequence.

Synthesis of Fluorenes and Dibenzo[ g,p]chrysenes through an Oxidative Cascade

We have developed robust, operationally simple syntheses of fluorenes and of dibenzo[g,p]chrysenes through oxidative cascade processes. These structures that are commonly encountered in optoelectronic materials, dyes, and pharmaceutical products are acces

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex

We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.