54495-62-4

Upstream product

• 108-39-4 3-methyl-phenol 
• 1077-02-7 3-methylphenyl methanesulfonate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 23530-43-0 2-(N,N-dimethylaminosulfonyl)nitrobenzene 

Downstream Products

• 60287-96-9 3-methyldibenzo[b,f][1,4]oxazepine 
• 227275-01-6 3-(2-nitro-phenoxy)-benzoic acid methyl ester 
• 206262-18-2 2-m-tolyloxy-benzenesulfonyl chloride 
• 27237-20-3 3-(2-nitro-phenoxy)-benzoic acid 
• 60287-67-4 2-m-tolyloxy-aniline 

Relevant academic research and scientific papers

Ligand-free copper-catalyzed O-arylation of arenesulfonamides with phenols: An unusual approach to biaryl ether synthesis

An unprecedented ligand-free copper-catalyzed O-arylation of arenesulfonamides with phenols has been developed. Thus, a range of unsysmmetric biaryl ethers were synthesized in excellent yields. The reaction occurs efficiently with excellent regioselectivity through the cleavage of Cary–S bond and with a good tolerance of functional groups on the phenyl ring of phenols. The reaction is appreciated for its readily accessible substrates, mild conditions, and simple operation under air.

Design, synthesis and antifungal activity of novel furancarboxamide derivatives

Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.

Additivity of substituent effects in aromatic stacking interactions

The goal of this study was to experimentally test the additivity of the electrostatic substituent effects (SEs) for the aromatic stacking interaction. The additivity of the SEs was assessed using a small molecule model system that could adopt an offset face-to-face aromatic stacking geometry. The intramolecular interactions of these molecular torsional balances were quantitatively measured via the changes in a folded/unfolded conformational equilibrium. Five different types of substituents were examined (CH3, OCH3, Cl, CN, and NO2) that ranged from electron-donating to electron-withdrawing. The strength of the intramolecular stacking interactions was measured for 21 substituted aromatic stacking balances and 21 control balances in chloroform solution. The observed stability trends were consistent with additive SEs. Specifically, additive SE models could predict SEs with an accuracy from ±0.01 to ±0.02 kcal/mol. The additive SEs were consistent with Wheeler and Houk's direct SE model. However, the indirect or polarization SE model cannot be ruled out as it shows similar levels of additivity for two to three substituent systems, which were the number of substituents in our model system. SE additivity also has practical utility as the SEs can be accurately predicted. This should aid in the rational design and optimization of systems that utilize aromatic stacking interactions.

Betti base as an efficient ligand for copper-catalyzed ullmann coupling of phenol with aryl halides

GRAPHICAL ABSTRACT A simple, general, and highly efficient Betti base ligand has been developed for copper-catalyzed Ullmann coupling of phenol with aryl halides without the protection of an inert atmosphere. The reaction proceeds smoothly in the presence of K2CO3 as the base and dimethylsulfoxide as the solvent. The catalyst was reused several times with no evident loss of catalytic activity and is environmentally friendly.

Microwave-assisted construction of diaryl ethers directly from arylmethanesulfonates as convenient latent phenols with aryl halides

The microwave-assisted synthesis of diaryl ethers directly from aryl halides and arylmethanesulfonates, which as latent phenols obviate a deprotection step prior to the SNAr reaction, in the presence of Cs2CO3 is described. The reaction time was very short (6-9-min), and good to excellent yields (53-90%) with the wide substrate scope were achieved without any catalyst. Copyright Taylor & Francis Group, LLC.

One-pot microwave-assisted tandem deprotection of arylmethanesulfonates / SNAr reaction for K2CO3-mediated C(aryl)-O bond formation

One-pot microwave-assisted tandem deprotection of arylmethanesulfonates / nucleophilic aromatic substitution reaction (SNAr) with activated aryl halides to synthesize asymmetrical diaryl ethers is described.

C(aryl)-O bond formation from aryl methanesulfonates via consecutive deprotection and SNAr reactions with aryl halides in an ionic liquid

An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methanesulfonates and a nucleophilic aromatic substitution (SNAr) with activated aryl halides.

Structure-based design of caspase-1 inhibitor containing a diphenyl ether sulfonamide

A series of compounds was designed and prepared as inhibitors of interleukin-1β converting enzyme (ICE), also known as caspase-1. These inhibitors, which employ a diphenyl ether sulfonamide, were designed to improve potency by forming favorable interactions between the diphenyl ether rings and the prime side hydrophobic region. An X-ray crystal structure of a representative member of the diphenyl ether sulfonamide series bound to the active site of caspase-1 was obtained.

Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6: Expansion of scope and utility

An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the S(N)Ar addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable 3- chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.