2432-11-3

Usage

Uses

Used in Chemical Synthesis:
2,6-Diphenylphenol is used as a ligand during the synthesis of reduced coordination (less than 6), unchelated manganese oxygen cluster systems. Its role in this process is crucial for the formation of these complex systems, which have potential applications in various industrial and research settings.
Used in Pharmaceutical and Chemical Industries:
In the preparation of derivatives of pyrazine-2,3-dicarbonitrile, 2,6-Diphenylphenol serves as a precursor required for the synthesis of octaazaphthalocyanine (AzaPc) derivatives. These AzaPc derivatives have potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapeutic agents.
Used in Coordination Chemistry:
2,6-Diphenylphenol is utilized as a building block in the creation of various coordination compounds. Its ability to form complexes with different metals contributes to the development of new materials with unique properties and potential applications in areas such as catalysis, sensing, and energy storage.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2784, 1986 DOI: 10.1021/jo00364a031

Upstream product

• 101-84-8 diphenylether 
• 1623-99-0 phenyl sodium 
• 24344-21-6 2,6-bis(1-cyclohexenyl)cyclohexanone 
• 71-43-2 benzene 
• 6738-04-1 2-phenoxy-1,1'-biphenyl 
• 102342-18-7 2,7-diphenyloxepin 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 90-43-7 2-Phenylphenol 
• 10368-54-4 2,6-diphenyl-1,4-benzoquinone diazide 
• 67-63-0 isopropyl alcohol 
• 108-95-2 phenol 
• 108-86-1 bromobenzene 
• 102342-19-8 1,6-diphenyl-trans-3,4-dibromo-7-oxabicyclo<4.1.0>heptane 
• 3293-32-1 2,6-dicyclohexylidenecyclohexanone 

Downstream Products

• 92-94-4 [1,1';4',1'']terphenyl 
• 3550-01-4 1,5,1',5'-tetraphenyl-[3,3']bicyclohexa-1,4-dienylidene-6,6'-dione 
• 124786-91-0 2,6-Diphenyl-4,4'-(1-methylethylidene)bisphenol 
• 124786-92-1 2,2',6,6'-Tetraphenyl-4,4'-(1-methylethylidene)bisphenol 
• 2887-97-0 2,6-diphenyl-[1,4]benzoquinone 
• 135505-61-2 1,3-Diphenyl-2-(phenylmethoxy)benzene 
• 57196-29-9 5'-[9-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-9H-fluoren-9-yl]-[1,1';3',1'']terphenyl-2'-ol 

Relevant academic research and scientific papers

The effect of topologically controlled coulombic interactions on the regioselectivity of the reductive cleavage of alkyl phenyl ethers

The importance of electrostatic effects in the chemical evolution of charged intermediates of the radical anion type is demonstrated. Thus, the regioselectivity of the electron transfer-induced reductive cleavage of alkyl 2,6-diphenylphenyl ethers and alkyl 2,6-dimethoxyphenyl ethers is completely reversed when a positive charge is placed in a controlled manner near the alkyl ether bond.

Probing Through-Space Polar-π Interactions in 2,6-Diarylphenols

Although it is well established that the acidity of phenol can be fine-tuned with substituents on its aromatic ring via through-bond effects, the role of through-space effects on the acidity of phenols is presently poorly understood. Here, we present integrated experimental and computational studies on substituted 2,6-diarylphenols that demonstrate the essential contribution from through-space OH -π interactions and O--π interactions in the observed trends in proton affinities and acidities of 2,6-diarylphenols.

Through-Space Polar-π Interactions in 2,6-Diarylthiophenols

Molecular recognition between polar groups and aromatic molecules is fundamentally important to rational drug design. Although it has been well established that many polar functionalities interact with electron-rich aromatic residues through energetically favorable polar-π interactions, there is a limited understanding of the association between thiols and aromatic systems. Herein we report physical-organic chemistry studies on 2,6-diarylthiophenols that possess the central thiophenol ring and two flanking aromatic rings with tunable electronic properties caused by substituents at distant para position. Hammett analysis revealed that pKa values and proton affinities correlate well with Hammett sigma values of substituents. Additional energy decomposition analysis supported the conclusion that both through-space SH-π interactions and S?-π interactions contribute to intramolecular stabilization of 2,6-diarylthiophenols.

Synergetic catalytic effect of rGO, Pd, Fe3O4 and PPy as a magnetically separable and recyclable nanocomposite for coupling reactions in green media

In this paper, rGO/Pd–Fe3O4@PPy as an efficient stable nanocomposite was synthesized. To understand the synergetic effects of rGO, Pd, Fe3O4 and PolyPyrrole, the performance of rGO/Pd–Fe3O4@PPy as a heterogeneous recyclable nanocatalyst in the green synthesis of C-C and C-O coupling products, as well as different conditions are studied. Synthesized rGO/Pd–Fe3O4@PPy was characterized by FT-IR, XRD, FE-SEM, EDS, TGA and AFM analysis. Best results are obtained under sonication in H2O for C-C coupling and by ball-milling for C-O coupling. The benefits of this method include: green solvents and conditions, absence of external base, low reaction times with high yield and easy work-up method.

Palladium-Catalyzed Reductive [5+1] Cycloaddition of 3-Acetoxy-1,4-enynes with CO: Access to Phenols Enabled by Hydrosilanes

A new palladium-catalyzed reductive [5+1] cycloaddition of 3-acetoxy-1,4-enynes with CO, enabled by hydrosilanes, has been developed for delivering valuable functionalized phenols. This methodology employs hydrosilanes as the external reagent to facilitate the [5+1] carbonylative benzannulation. The reaction is a conceptually and mechanistically novel carbonylative cycloaddition route for the construction of substituted phenols, through the formation of four new chemical bonds, with excellent functional-group tolerance.

Preparation method of multi-substituted phenol

The invention provides a preparation method of multi-substituted phenol. According to the preparation method, raw materials, namely alkyl ketone and alkene, are subjected to condensation-aromatizationunder action of a catalyst to obtain multi-substituted phenol. Compared with the prior art, the preparation method has the advantages that the raw materials are easy to obtain, the yield is high, cost is low since use of expensive metallic catalysts is avoided, and the preparation method is suitable for industrial production and the like.

Preparation method of 2,6-diphenylphenol

The invention relates to a preparation method of 2,6-diphenylphenol. The preparation method comprises the following step: carrying out Suzuki coupling reaction on 2,6-dichlorophenol and phenylboronic acid used as raw materials by using palladium acetate and a phosphine ligand as catalysts to obtain the compound 2,6-diphenylphenol. Compared with the prior art, the method has the advantages of simple preparation technique, common and accessible catalysts, high product purity and high, simple and safe operational process and low raw material cost, and is beneficial to industrial production.

P(NMe2)3-promoted ortho-selective arylation of phenols with diaryliodonium triflates via rhodium catalysis

Rh-catalyzed ortho-selective arylation of free phenol with diaryliodonium triflates to widely existed phenol-containing biaryls have been developed. The use of P(NMe2)3, tBuOLi and CH3CN proved to be critical for the ortho-selectivity of this reaction.

A New Route to Phenols: Palladium-Catalyzed Cyclization and Oxidation of γ,δ-Unsaturated Ketones

We report a new strategy for the synthesis of phenols from acyclic unsaturated ketones in one pot. The reaction proceeds by palladium-catalyzed carbopalladation of an alkene with the enol form of the tethered ketone, generating a substituted cyclohexanone. Upon introduction of a terminal oxidant a palladium-catalyzed oxidation ensues to give the desired phenol. This approach allows the programming of phenol substituents on the acyclic substrate and therefore circumvents the limitations inherent in traditional syntheses of phenols.

Highly practical iron-catalyzed C-O cleavage reactions

Facile iron-catalyzed cleavage of various allyl, cinnamyl and benzyl C-O linkages has been effected in the presence of ethylmagnesium chloride. The protocol is operationally simple (xylene-THF, r.t., 1 h), requires low catalyst loading (1 mol% FeCl2) and tolerates halides, esters, amines, ethers and olefins. The allyl moiety is converted to volatile hydrocarbons which renders laborious product separation unnecessary.