946-80-5

Usage

Uses

Used in Catalytic Chemistry:
Benzyl phenyl ether is used as a model compound for studying the α-O4 ether bond in lignin and coal. It helps researchers understand the reaction pathways and mechanisms involved in the catalytic conversion of these complex materials.
Used in Biomass Conversion:
Benzyl phenyl ether is used in the study of biomass conversion processes, particularly in the investigation of the influence of alkali carbonates, which are common additives in biomass conversion. The reaction pathways of benzyl phenyl ether in superheated water have been reported, providing insights into the conversion of lignin and coal.
Used in the Production of Aromatics:
Benzyl phenyl ether is used in the investigation of cesium-exchanged heteropolyacid catalyzed decomposition to produce aromatics. This research is important for developing efficient methods to convert lignin and coal into valuable chemical products.
Used in Photo-Claisen Rearrangements:
Benzyl phenyl ether is used in the study of photo-Claisen rearrangements in cation-exchanged Y zeolites and polyethylenes of differing crystallinities. This research contributes to the understanding of the rearrangement reactions and their potential applications in the synthesis of various organic compounds.
General Description:
Benzyl phenyl ether is a light brown-orange chunky substance, which is a reactive organic oxygenate containing an ether functional group. It is present in subbituminous and bituminous coals and is a useful model compound for studying the α-O4 ether bond in lignin and coal. Its weak ether bond of 234 kJ/mol makes it one of the most thermo-labile compounds in lignin and low-rank coal.

InChI:InChI=1/C13H12O/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13/h1-10H,11H2

Upstream product

• 93-99-2 benzoic acid phenyl ester 
• 139-02-6 sodium phenoxide 
• 3204-68-0 benzyldimethylphenylammonium chloride 
• 100-39-0 benzyl bromide 
• 64-17-5 ethanol 
• 100-67-4 potassium phenolate 
• 100-44-7 benzyl chloride 
• 135023-64-2 sulfurous acid monophenyl ester; sodium-salt 
• 108-88-3 toluene 
• 108-95-2 phenol 
• 2876-13-3 N-benzylpyridinium chloride 
• 100-66-3 methoxybenzene 
• 102-09-0 bis(phenyl) carbonate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 108-88-3 toluene 
• 108-95-2 phenol 
• 100-52-7 benzaldehyde 
• 6793-92-6 p-benzyloxyphenylbromide 
• 834-14-0 p-benzylanizole 
• 36441-31-3 1-benzyl-2-naphthol 
• 51010-48-1 1-methoxy-4-benzylnaphthalene 
• 36438-64-9 p-benzyloxystyrene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 91-20-3 naphthalene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 95-13-6 1-indene 
• 211-16-5 benzo[1,2-c:3,4-c']bis(1,2,5)thiadiazole 
• 135505-51-0 N,N-Diphenyl-1-naphthalenemethanamine 

Relevant academic research and scientific papers

Visible light mediated synthesis of 6H-benzo[c]chromenes: transition-metal-free intramolecular direct C-H arylation

A synthetic approach towards the 6H-benzo[c]chromene ring under visible light and transition-metal-free conditions has been developed. Benzochromenes are synthesized from the corresponding (2-halobenzyl) phenyl ethers or (2-halophenyl) benzyl ethers using

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

A Bottleable Imidazole-Based Radical as a Single Electron Transfer Reagent

Reduction of 1,3-bis(2,6-diisopropylphenyl)-2,4-diphenyl-1H-imidazol-3-ium chloride (1) resulted in the formation of the first structurally characterized imidazole-based radical 2. 2 was established as a single electron transfer reagent by treating it with an acceptor molecule tetracyanoethylene. Moreover, radical 2 was utilized as an organic electron donor in a number of organic transformations such as in activation of an aryl-halide bond, alkene hydrosilylation, and in catalytic reduction of CO2 to methoxyborane, all under ambient temperature and pressure.

SOLVENT-FREE CROSS-COUPLING REACTION, AND PRODUCTION METHOD USING SAID REACTION

Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group;preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; andperforming a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.

Direct Deamination of Primary Amines via Isodiazene Intermediates

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents

The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.

Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols

A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.

Method for synthesizing aryl benzyl ether compound

The invention discloses a method for synthesizing aryl benzyl ether compounds, which comprises the following steps: by using an iron (III) complex containing 1, 3-di-tert-butyl imidazole cations and having a molecular formula of [(tBuNCH = CHNtBu) CH] [FeBr4] as a catalyst and di-tert-butyl peroxide as an oxidant, carrying out oxidative coupling reaction on phenolic compounds and toluene compounds to synthesize the corresponding aryl benzyl ether compounds. The method is the first example for preparing the aryl benzyl ether compound through the oxidative coupling reaction of the phenolic compound and the toluene compound, which is realized by an iron-based catalyst, and has the advantages of atom economy, environmental friendliness and good substrate applicability.

Application of iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds

The invention discloses an application of an iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds, and particularly relates to a method for synthesizing corresponding aryl benzyl ether compounds by taking di-tert-butyl peroxide as an oxidizing agent and carrying out oxidative coupling reaction on phenolic compounds and toluene compounds. According to the method, the iron (III) complex is used as the catalyst for the first time, and oxidative coupling of the phenolic compound and the toluene compound is realized. The method is the first oxidative coupling reaction of phenolic compounds and benzyl C(sp3)-H bonds, and a new method is provided for synthesizing aryl benzyl ether compounds. Compared with an existing synthesis method, the method provided by the invention avoids using toxic and polluting halogenated hydrocarbon and strong base, has better atom economy, and conforms to the development concept of green synthetic chemistry.

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.