20927-98-4

Usage

Uses

Used in Chemical Synthesis:
2-(p-Tolyloxy)aniline is used as an intermediate in the synthesis of various dyes and pigments, contributing to the coloration and stability of these products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-(p-Tolyloxy)aniline is utilized as a building block for the development of new drugs, leveraging its structural properties to create novel therapeutic agents.
Used in Organic Reactions:
2-(p-Tolyloxy)aniline also plays a role in organic reactions, where it can be transformed into different chemical entities, expanding the scope of organic chemistry and material science.
Used in Material Development:
The presence of the para-tolyl group in 2-(p-Tolyloxy)aniline makes it a valuable precursor in the development of new materials, potentially enhancing their properties and applications in various industries.

InChI:InChI=1/C13H13NO/c1-10-6-8-11(9-7-10)15-13-5-3-2-4-12(13)14/h2-9H,14H2,1H3

Upstream product

• 106-44-5 p-cresol 
• 1192-96-7 potassium p-cresolate 
• 577-19-5 2-nitrophenyl bromide 
• 88-73-3 2-Chloronitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 3402-70-8 1-nitro-2-(p-tolyloxy)benzene 

Downstream Products

• 128643-14-1 N-[2-(4-methylphenoxy)phenyl]acetamide 
• 133437-36-2 [1-Phenyl-meth-(E)-ylidene]-(2-p-tolyloxy-phenyl)-amine 
• 1436919-26-4 1-(p-tolyloxy)-2-(2-phenylethynyl)benzene 
• 106-49-0 p-toluidine 
• 133437-35-1 2-benzylamino-4'-methyldiphenyl ether 
• 87671-67-8 2-[(4-methylphenyl)amino]phenol 
• 76840-94-3 Imidazolidin-2-ylidene-(2-p-tolyloxy-phenyl)-amine 
• 76839-01-5 (2-p-Tolyloxy-phenyl)-thiourea 

Relevant academic research and scientific papers

NOVEL TRIAZINE COMPOUND, AND ORGANIC ELECTRONIC ELEMENT AND PLANT-GROWING LIGHTING THAT USE THE SAME

PROBLEM TO BE SOLVED: To provide a triazine compound which has a high triplet energy level and excellent heat resistance, and can be used as an organic electronic element material realizing an element with high efficiency, low voltage and a long life. SOLUTION: In the triazine compound, as represented by the general formula [1] in the figure, a triazine backbone moiety is linked to a dibenzofuran or dibenzothiophene backbone moiety via a biphenyl backbone moiety, where X is an oxygen atom or sulfur atom. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed dehydrogenative C-H activation/annulation

In this report, we have described a FeCl3-catalyzed process involving intramolecular annulation of o-phenoxy diarylacetylenes via hydroarylation to afford a series of biologically potent fused seven-membered (6-7-6) ring compounds under mild reaction conditions. This reaction was believed to proceed through Friedel-Crafts type sequential carbometallation followed by protonation to produce phenyldibenz[b,f]oxepines. This method was also extended to synthesize seven-membered rings that are fused with coumarins.

Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.

Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches

A highly efficient palladium-catalyzed fourfold tandem-domino reaction consisting of two carbopalladation and two C-H-activation steps was developed for the synthesis of two types of tetrasubstituted alkenes 3 and 6 with intrinsic helical chirality starting from substrates 1 and 4, respectively. A sixfold tandem-domino reaction was also developed by including a Sonogashira reaction. 20 compounds with different substitution patterns were prepared with yields of up to 97%. Structure elucidation by X-ray crystallography confirmed helical chirality of the two alkene moieties. Photophysical investigations of some of the compounds showed pronounced switching properties through light-controlled changes of their stereochemical configuration.

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.

Synthesis and enantioselective hydrogenation of seven-membered cyclic imines: Substituted dibenzo[b,f][1,4]oxazepines

Highly enantioselective hydrogenation of seven-membered cyclic imines, substituted dibenzo[b,f][1,4]oxazepines, was achieved, with up to 94% ee, by using the [Ir(COD)Cl]2/(S)-Xyl-C3*-TunePhos complex as the catalyst in the presence of morpholine-HCl.

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.

An improved synthesis of dibenzofurans by a free-radical cyclization

Reaction conditions for the formation of dibenzofurans from diazotized o-(aryloxy)anilines have been examined. Several promoters (hydroquinone, SnCl2, NaI, CuSO4, FeSO4, etc.) have been discovered; these act as electron donors and promote a free-radical mechanism. The best of these is FeSO4 which shortens the reaction time from hours to minutes and contributes to high yields (77-83%). We have been able to transform the cyclization to a reliable and convenient synthesis.