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Usage

Uses

Used in Pharmaceutical Industry:
4-(2-aminophenoxy)benzonitrile is used as a key intermediate for the synthesis of various pharmaceutical compounds, leveraging its unique chemical structure to contribute to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(2-aminophenoxy)benzonitrile is utilized as a building block in the creation of agrochemicals, potentially enhancing the effectiveness of pesticides and other agricultural chemicals.
Used in Organic Chemistry:
4-(2-aminophenoxy)benzonitrile serves as a valuable component in organic chemistry, where it is employed in the synthesis of complex organic molecules, contributing to the advancement of chemical research and development.
Used in Material Science:
4-(2-aminophenoxy)benzonitrile is used as a precursor in the development of functional materials, such as liquid crystals, which have applications in display technologies and other advanced material systems.
These applications highlight the diverse utility of 4-(2-aminophenoxy)benzonitrile across different fields, underscoring its importance in both research and industrial applications.

Upstream product

• 113344-23-3 4-(2-nitrophenoxy)benzonitrile 
• 1493-27-2 ortho-nitrofluorobenzene 
• 767-00-0 4-cyanophenol 

Downstream Products

• 76838-23-8 1-Benzoyl-3-[2-(4-cyano-phenoxy)-phenyl]-thiourea 
• 76840-98-7 4-[2-(Imidazolidin-2-ylideneamino)-phenoxy]-benzonitrile 
• 76839-04-8 [2-(4-Cyano-phenoxy)-phenyl]-thiourea 

Relevant academic research and scientific papers

Discovery of Benzamidine- And 1-Aminoisoquinoline-Based Human MAS-Related G-Protein-Coupled Receptor X1 (MRGPRX1) Agonists

Mas-related G-protein-coupled receptor X1 (MRGPRX1) is a human sensory neuron-specific receptor and has been actively investigated as a therapeutic target for the treatment of pain. By use of two HTS screening hit compounds, 4-(4-(benzyloxy)-3-methoxybenzylamino)benzimidamide (5a) and 4-(2-(butylsulfonamido)-4-methylphenoxy)benzimidamide (11a), as molecular templates, a series of human MRGPRX1 agonists were synthesized and evaluated for their agonist activity using HEK293 cells stably transfected with human MrgprX1. Conversion of the benzamidine moiety into a 1-aminoisoquinoline moiety carried out in the later stage of structural optimization led to the discovery of a highly potent MRGPRX1 agonist, N-(2-(1-aminoisoquinolin-6-yloxy)-4-methylphenyl)-2-methoxybenzenesulfonamide (16), not only devoid of positively charged amidinium group but also with superior selectivity over opioid receptors. In mice, compound 16 displayed favorable distribution to the spinal cord, the presumed site of action for the MRGPRX1-mediated analgesic effects.

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.