3933-94-6

Usage

Uses

Used in Chemical Industry:
4-PHENOXYBIPHENYL is used as an intermediate in the production of liquid crystals for its ability to contribute to the formation of stable liquid crystal structures.
Used in Pharmaceutical Industry:
4-PHENOXYBIPHENYL is used as a precursor in the synthesis of other chemical compounds, potentially for the development of pharmaceuticals or other health-related products.
Used in Regulatory Scrutiny:
4-PHENOXYBIPHENYL is used as a subject of regulatory scrutiny due to its classification as a substance of very high concern by the European Chemicals Agency, as it exhibits estrogenic activity and has potential health concerns.
Used in Research and Development:
4-PHENOXYBIPHENYL is used in research and development efforts to find alternative chemicals for its various industrial applications, given the health concerns and regulatory restrictions associated with its use.

Upstream product

• 92-66-0 4-bromo-1,1'-biphenyl 
• 108-95-2 phenol 
• 116016-75-2 diphenylytterbium 
• 106-51-4 p-benzoquinone 
• 108-86-1 bromobenzene 
• 92-69-3 4-Phenylphenol 
• 7005-72-3 4-chlorodiphenyl ether 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 150-76-5 4-methoxy-phenol 
• 591-50-4 iodobenzene 
• 101-55-3 4-Bromodiphenyl ether 
• 35155-10-3 potassium [1,1'-biphenyl]-4-olate 
• 1591-31-7 4-iodo-biphenyl 

Downstream Products

• 110-85-0 piperazine 
• 92-52-4 biphenyl 
• 92-69-3 4-Phenylphenol 
• 6093-03-4 [1,1′:3′,1″-terphenyl]-4′-ol 
• 4731-97-9 2-(1,1'-biphenyl-4-yl)phenol 
• 7535-20-8 1-p-Acetylphenyl-4-p-acetylphenoxybenzol 
• 10466-52-1 1-{4'-[4-(3-Oxo-butyryl)-phenoxy]-biphenyl-4-yl}-butane-1,3-dione 
• 35155-09-0 4-(biphenyl-4'-yloxy)acetophenone 
• 108-95-2 phenol 
• 92-94-4 [1,1';4',1'']terphenyl 
• 31708-14-2 1-cyclohexyl-1H-pyrrole 
• 4096-21-3 N-phenylpyrrolidine 
• 169963-54-6 4-(morpholino)biphenyl 
• 827-52-1 1-phenyl-1-cyclohexane 

Relevant academic research and scientific papers

Unexpected activation of carbon-bromide bond promoted by palladium nanoparticles in Suzuki C-C couplings

Dihydroanthracene derivatives (1-6) containing imide (1-3) and amine (4-6) functions have been used for the stabilization of palladium nanoparticles, starting from Pd(0) and Pd(ii) organometallic precursors. Well-dispersed nanoparticles of mean size in the range ca. 1.9 to 3.6 nm could be obtained using Pd(0) precursors (PdLc and PdLd, where L = 1-6 and c and d mean the organometallic precursor involved, [Pd2(dba)3] and [Pd(ma)(nbd)] respectively). With the aim to evaluate the behaviour of homogeneous species and nanoparticles used as catalytic precursors, palladium complex coordinated to the diamine 6, [Pd(OAc)2(κ2- N,N-6)], was prepared, reporting for the first time the X-ray diffraction structure of a metallic complex containing a ligand with a 9,10- dihydroanthracene backbone. Palladium systems were evaluated in Suzuki C-C coupling reactions and relevant differences were observed comparing the reactivity of the homogeneous systems in relation to that obtained using palladium nanoparticles as starting catalyst in relation to the activation of the C-Br bonds for deactivated substrates.

Silver nanoparticles doped TiO2 catalyzed Suzuki-coupling of bromoaryl with phenylboronic acid under visible light

The formation of the carbon?carbon bond in the synthetic chemistry explored in many ways. Suzuki-cross coupling is one of the ways to make bonds between two carbon atoms of similar molecules or different molecules. C–C bond was successfully formed between two aryl rings of aryl halides and phenylboronic acid at room temperature and atmospheric pressure under the visible illuminance. In this work we report, an in-situ synthesis of silver nanoparticles doped TiO2 nanoparticles (NPs) and studied its catalytic activity as an eco-friendly, simple, recyclable and efficient catalyst for one-pot Suzuki-coupling of bromoaryl with phenylboronic acid under visible light. Only, 45 mg of the catalyst resulted in a 98% conversion of p-ethyl bromobenzene with a 97% yield of p-ethyl biphenyl using toluene as the solvent in the presence of visible light at atmospheric pressure. The electron-donating groups (e.g., ethyl group) substituted bromobenzene resulted in the maximum yields than that of the substitution with the electron-withdrawing groups. The catalyst shown significant catalytic activity up to seven recycling runs without any loss. The doping of silver nanoparticles boosted the catalytic activity at titanium dioxide surface as well as inside the pores. The high surface area of the semiconductor support provides the sites for accommodated silver nanoparticles and shows enhanced reactivity towards the coupling reaction of bromoaryl with phenylboronic acid. The as-synthesized catalyst was thoroughly characterized by XRD, TEM, EDX, XPS, FTIR, TGA, UV–vis, Raman and BET analysis. The high recyclability of the photocatalyst remarked the footprints in the C–C coupling reactions.

Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates

High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.

Nickel-Catalyzed Etherification of Phenols and Aryl Halides through Visible-Light-Induced Energy Transfer

Notwithstanding some progress in nickel-catalyzed etherification of alkanols and arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one as the photosensitizer under visible light. This photocoupling exhibits a broad substrate scope.

Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates

A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.

Green and sustainable palladium nanomagnetic catalyst stabilized by glucosamine-functionalized Fe3O4@SiO2 nanoparticles for Suzuki and Heck reactions

A novel magnetic and heterogeneous palladium-based catalyst stabilized by glucosamine-functionalized magnetic Fe3O4@SiO2 nanoparticle was synthesized. The strategy relies on the covalently bonding of glucosamine to cyanuric chloride-functionalized magnetic nanoparticles followed by complexation with palladium. The structure of magnetic nanocatalyst was fully determined by FT-IR, XRD, DLS, FE-SEM, TEM, ICP, UV-Vis, TGA, VSM, and EDX. The obtained results confirmed that the palladium nanoparticles stabilized by glucosamine immobilized onto the magnetic support exhibited high activity in cross-coupling reactions of Suzuki-Miyaura and Mizoroki-Heck. Various aryl halides were coupled with arylboronic acid (Suzuki cross-coupling reaction) and olefins (Heck reactions) under the green conditions to provide corresponding products in high to excellent yields. Interestingly, the catalyst can be easily isolated from the reaction media by magnetic decantation and can subsequently be applied for consecutive reaction cycles (at least seven times) with no notable reduction in the catalytic activity.

Bis(NHC)-Pd-catalyzed one-pot competitive C-C*C-C, C-C*C-O, C-C*C-N, and C-O*C-N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions

Bis(NHC)-Pd-catalyzed competitive asymmetrical C-C*C-C, C-C*C-O, C-C*C-N, and O-C*C-N cross-coupling reactions were performedviathe one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anionsviaa Hofmann elimination on a 1,3,5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C-C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C-N and C-O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.

Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates

A metal-free route for the synthesis of biarenes has been developed. The approach is based on the photoextrusion of a phosphate moiety occurring upon irradiation of biaryl- A nd triaryl phosphates. The reaction involves an exciplex as the intermediate and it is especially suitable for the preparation of electron-rich biarenes.

Immobilized Pd on a NHC functionalized metal–organic framework MIL-101(Cr): an efficient heterogeneous catalyst in Suzuki?Miyaura coupling reaction in water

A novel Pd?NHC functionalized metal–organic framework (MOF) based on MIL-101(Cr) was synthesized and used as an efficient heterogeneous catalyst in the C-C bond formation reactions. Using this heterogeneous Pd catalyst system, the Suzuki?Miyaura coupling reaction was accomplished well in water, and coupling products were obtained in good to excellent yields in short reaction time. The Pd?NHC?MIL-101(Cr) was characterized using some different techniques, including Fourier transform-infrared, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy (TEM), X-ray photoelectron spectroscopy, inductively coupled plasma and elemental analysis. The microscopic techniques showed the discrete octahedron structure of MIL-101(Cr), which is also stable after chemical modification process to prepare the catalyst system. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the structure of the catalyst, while no reducing agent was used. It seems that the NHC groups and imidazolium moieties in the structure of the MOF can reduce Pd (II) to Pd (0) species. This modified MOF substrate can also prevent aggregation of Pd nanoparticles, resulting in high stability of them in organic transformation. The Pd?NHC?MIL-101(Cr) catalyst system could be simply extracted from the reaction mixture, providing an efficient synthetic method for the synthesis of biaryls derivatives using the aforementioned coupling reaction. The Pd?NHC?MIL-101(Cr) catalyst could be recycled in this organic reaction with almost consistent catalytic efficiency.

Nickel(ii) N-heterocyclic carbene complexes as efficient catalysts for the Suzuki—Miyaura reaction

Catalytic activity of nickel(ii) and palladium(ii) N-heterocyclic carbene (NHC) complexes derived from imidazole, benzimidazole, and 1,2,4-triazole was comparatively evaluated in the cross-coupling reactions of aryl halides with arylboronic acids. Readily available nickel bis-NHC complexes (NHC)2NiX2 (X = Cl, Br, or I) exhibited the activity comparable to that of the structurally related palladium complexes and, consequently, can be applied as efficient catalysts for the Suzuki—Miyaura reaction.