6738-04-1

Basic information

• Product Name: 2-PHENOXYBIPHENYL
• Synonyms: O-DIPHENYL PHENYL ETHER;2-PHENOXYBIPHENYL;2-BIPHENYLYLPHENYL ETHER;2-BIPHENYL PHENYL ETHER;2-PHENYLOXYBIPHENYL;2-Phenoxy-1,1'-biphenyl;2-Phenoxydiphenyl;Ether, 2-biphenylyl phenyl
• CAS NO: 6738-04-1
• Molecular Formula: C₁₈H₁₄O
• Molecular Weight: 246.3
• EINECS: 229-793-3
• Product Categories: Biphenyl derivatives
• Mol File: 6738-04-1.mol

Chemical Properties

• Melting Point: 48-50°C
• Boiling Point: 200-201 °C
• Appearance: /
• Density: 1.093
• BRN: 2371408
• CAS DataBase Reference: 2-PHENOXYBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENOXYBIPHENYL(6738-04-1)
• EPA Substance Registry System: 2-PHENOXYBIPHENYL(6738-04-1)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 6738-04-1(Hazardous Substances Data)

Usage

Uses

Used in Liquid Crystal Synthesis:
2-Phenoxybiphenyl is used as a starting material in the synthesis of liquid crystal compounds. Its unique molecular structure contributes to the formation of liquid crystals, which have various applications in display technologies and other industries.
Used in Polymeric Material Production:
2-Phenoxybiphenyl is used as a component in the production of polymeric materials. Its incorporation into polymers can enhance their properties, such as thermal stability and mechanical strength, making them suitable for various applications.
Used in Pharmaceutical Research:
2-Phenoxybiphenyl has been investigated for its potential use in pharmaceuticals. Its unique chemical structure may offer new opportunities for drug development, although further research is needed to explore its therapeutic potential.
Used in Agrochemical Development:
2-Phenoxybiphenyl has also been studied for its potential applications in agrochemicals. Its chemical properties may be harnessed to develop new pesticides or other agricultural chemicals to improve crop protection and yield.

InChI:InChI=1/C18H14O/c1-3-9-15(10-4-1)17-13-7-8-14-18(17)19-16-11-5-2-6-12-16/h1-14H

Upstream product

• 2113-51-1 2-iodobiphenyl 
• 100-67-4 potassium phenolate 
• 101-84-8 diphenylether 
• 108-90-7 chlorobenzene 
• 90-43-7 2-Phenylphenol 
• 1623-99-0 phenyl sodium 
• 71-43-2 benzene 
• 144190-64-7 bis(2,2'-biphenylylene)sulfurane 
• 108-95-2 phenol 
• 19615-37-3 bis(2,2'-bisphenylylene)selenurane 
• 108-86-1 bromobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 98-80-6 phenylboronic acid 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 90247-81-7 2,2''-oxydi-1,1'-biphenyl 
• 2432-11-3 (1,1';3',1''-terphenyl)-2'-ol 
• 92-52-4 biphenyl 
• 90-43-7 2-Phenylphenol 

Relevant articles and documents

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.

Diaryl Ether Formation Merging Photoredox and Nickel Catalysis

Photoredox and Ni catalysis are combined to produce diaryl ethers under mild conditions. A broad range of aryl halides and phenol derivatives are cross-coupled in the presence of a readily available organic photocatalyst and NiBr2(dtbpy). Symmetrical diaryl ethers have also been directly obtained from aryl bromides in the presence of water. Mechanistic investigations support the involvement of Ni(0) species at the outset of the reaction and a Ni(II)/Ni(III)-photocatalyzed single electron transfer process preceding the productive C(sp2)-OAr reductive elimination.

Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons

To date, cleavage of the C-N bond in aromatic amides has been achieved in molecules with a distorted constitutional framework around the nitrogen atom. In this report, a nickel-catalyzed reduction of planar amides to the corresponding lower hydrocarbon homologue has been reported. This involves a one-pot reductive cleavage of the C-N bond followed by a tandem C-CO bond break in the presence of a hydride source. Substrate scope circumscribes deamidation examples which proceed via oxidative addition of nickel in the amide bonds of nontwisted amides. Mechanistic studies involving isolation and characterization of involved intermediates via different spectroscopic techniques reveal a deeper introspection into the plausible catalytic cycle for the methodology.

The Suzuki-Miyaura Coupling of Nitroarenes

Synthesis of biaryls via the Suzuki-Miyaura coupling (SMC) reaction using nitroarenes as an electrophilic coupling partners is described. Mechanistic studies have revealed that the catalytic cycle of this reaction is initiated by the cleavage of the aryl-nitro (Ar-NO2) bond by palladium, which represents an unprecedented elemental reaction.

Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights

A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.

Visible-light-mediated synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts

With visible-light irradiation, a simple and metal-free photocatalytic system for the synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts has been developed. The reaction proceeded in high yield for a range of different substrates in the presence of eosin Y under mild reaction conditions.

General method for functionalized polyaryl synthesis via aryne intermediates

A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.

Synthesis of benzannulated heterocycles by twofold Suzuki-Miyaura couplings of cyclic diarylborinic acids

Two-fold Suzuki-Miyaura cross-couplings of cyclic diarylborinic acids are described. This novel annulation method enables the synthesis of benzo-fused heterocycles from dihaloarenes or gem-dibromoolefins.

Reactions of enantiopure cyclic diols with sulfuryl chloride

Monocyclic allylic cis-1,2-diols reacted with sulfuryl chloride at 0 °C in a regio- and stereo-selective manner to give 2-chloro-1-sulfochloridates, which were hydrolysed to yield the corresponding trans-1,2-chlorohydrins. At -78 °C, with very slow addition of sulfuryl chloride, cyclic sulfates were formed in good yields, proved to be very reactive with nucleophiles and rapidly decomposed on attempted storage. Reaction of a cyclic sulfate with sodium azide yielded a trans-azidohydrin without evidence of allylic rearrangement occurring. An enantiopure bicyclic cis-1,2-diol reacted with sulfuryl chloride to give, exclusively, a trans-1,2-dichloride enantiomer with retention of configuration at the benzylic centre and inversion at the non-benzylic centre; a mechanism is presented to rationalise the observation.

Solar energy assisted synthesis of palladium nanoplates and its application in 2-phenoxy-1,1′-biphenyls and N,N-dimethyl-[1,1′-biphenyl] derivatives synthesis

Present work aims to develop a greener approach for the palladium nanoplates (PdNPs) synthesis and its catalytic applications. The protocol deals with solar energy assisted ionic palladium reduction in the presence of polyvinylpyrrolidone (PVP) and ethylene glycol (EG) with a good shape selectivity. Polyvinylpyrrolidone plays a duel role of capping agent and mild reductant; whereas, ethylene glycol acts as a reductant and solvent. The optimum sunlight concentration is a key factor to the anticipated nanoplate's synthesis. Results show that the most of nanoparticles are hexagonal and triangular nanoplates in the range of 20-50 nm. This is a first report which shows ～70% selectivity to the nanoplates formation using sun light. The study also covers it's catalytic application, wherein; 2-phenoxy-1,1′- biphenyls and N,N-dimethyl-[1,1′-biphenyl] derivatives were synthesized by a simple, ligand free, faster, one pot, ecological and economic protocol in aqueous medium. The catalyst shows better performance than that of conventionally available 10% Pd/C catalyst. The prepared PdNPs showed excellent catalytic performance to the desired products with recyclability.