5098-99-7

Usage

Uses

Used in Organic Synthesis:
(4Z)-4-[(4-methylphenyl)hydrazono]naphthalen-1(4H)-one is utilized as a reagent in organic synthesis, playing a crucial role in the formation of various organic compounds. Its ability to participate in a range of chemical reactions makes it a valuable asset in this field.
Used in Medicinal Chemistry:
Possessing potential applications in medicinal chemistry, (4Z)-4-[(4-methylphenyl)hydrazono]naphthalen-1(4H)-one can be employed as a building block for the development of new pharmaceuticals. Its unique structure may contribute to the creation of novel drugs with improved efficacy and selectivity.
Used as a Dye Precursor:
In the chemical industry, (4Z)-4-[(4-methylphenyl)hydrazono]naphthalen-1(4H)-one serves as a precursor for the synthesis of dyes. Its chemical properties allow for the production of a variety of dye compounds, contributing to the diversity of colors available for various applications.
Used in Research and Development:
(4Z)-4-[(4-methylphenyl)hydrazono]naphthalen-1(4H)-one's unique structure and reactivity make it an essential tool in research and development, particularly in the fields of chemistry and materials science. It can be used to study reaction mechanisms, develop new synthetic methods, and explore novel applications in various industries.

Upstream product

• 90-15-3 α-naphthol 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 106-49-0 p-toluidine 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 130-15-4 [1,4]naphthoquinone 
• 36853-51-7 Naphthochinon-(1,4)-yl-<4-methyl-phenylhydrazon> 
• 57573-52-1 4-methylbenzene diazonium 

Downstream Products

• 71811-76-2 (4-methoxy-[1]naphthyl)-p-tolyl-diazene 
• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 
• 108-88-3 toluene 
• 130-15-4 [1,4]naphthoquinone 
• 36853-51-7 Naphthochinon-(1,4)-yl-<4-methyl-phenylhydrazon> 

Relevant academic research and scientific papers

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC50 (μg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 μg/mL) compared to the reference drug acarbose (21.59 ± 1.5 μg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a non-competitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.

Nano-Fe3O4 encapsulated-silica supported boron trifluoride as a novel heterogeneous solid acid for solvent-free synthesis of arylazo-1-naphthol derivatives

Nano-Fe3O4 encapsulated-silica supported boron trifluoride (Fe3O4@SiO2-BF3) as a new type of green heterogeneous solid acid was prepared by the immobilization of BF3·Et2O on the surface of Fe3O4@SiO2 core-shell nanoparticles and characterized by Fourier transform-infrared spectroscopy (FT-IR), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), field emission-scanning electron microscope (FE-SEM), energy dispersive X-ray (EDS), and transmission electron microscope (TEM). Then, this super solid acid was used as an acidic reagent for the synthesis of aryl diazonium salts as a starting reactant, followed by its diazo coupling with 1-naphthol in a basic solvent-free medium at room temperature. The main advantages of this clean method were high yields, short reaction times, the possibility of performing it at room temperature, and no need of corrosive and toxic liquid acids and solvents. In addition, the long-term stability of aryl diazonium salts supported on Fe3O4@SiO2-BF3 magnetic nanoparticles (MNPs) at room temperature was one of the most important results of this procedure. This journal is

Facile synthesis of 1-naphthol azo dyes with nano Sio2/Hio4 under solvent-free conditions

Nano-silica supported periodic acid (nano-SPIA) has been utilized as a heterogeneous reagent for a highly efficient and one pot synthesis of azo dyes based on 1-naphthol under solvent-free conditions at room temperature. This method has some advantages, the reaction workup is very easy and the catalyst can be easily separated from the reaction mixture and one-pot procedure. The related products have been obtained in good to excellent yields, high purity and short reaction times. The structures of the products have been characterized by several techniques using UV-Vis, FT-IR, 1H NMR, 13C NMR and mass spectra.

Synthesis and photochemical properties of cationic cyclopentadienyliron containing arylazo chromophores

Two kinds of cationic cyclopentadienyliron complexes containing arylazo chromophores (Azo-Fc) were synthesized through the nucleophilic aromatic substitution reactions of cyclopentadienyliron chlorobenzene complexes. The synthesized Azo-Fc was characterized by LC-MS, IR, and 1H NMR. The influence of substituents and the aryl ring on spectral data of the synthesized compounds is described. Unlike other cationic cyclopentadienyliron complexes, Azo-Fc hardly underwent photolysis and showed no photo-initiating abilities in the cationic polymerization under photo-irradiation; in addition, trans/cis isomerization by irradiation is possible at different wavelengths.

Solid state photolysis of triazene 1-oxides with naphthols. Synthesis of azo dyes

Sunlight irradiation of solid mixed crystals of the photolabile triazene 1-oxides and α- or β-naphthol afford azo dyes.

Photooxidation of Arylazo-Naphtholes with Singlet Oxygen

The reaction of p-substituted 4-arylazo-1-naphtholes 1 and 1-arylazo-2-naphtholes 5 with singlet oxygen (produced by methylene blue-sensitized photolysis) has been studied spectroscopically in methanol as a solvent.The rate constants of dye bleaching are the same, irrespective whether the extinctions of the azo or the hydrazone forms of the tautomeric systems are measured.Both reaction series 1 and 5 afford linear Hammett plots, which is discussed in the light of the azo-hydrazone equilibrium of the dyes and an "ene" mechanism of the reaction with singlet oxygen.It could be shown by short-time spectroscopy that the azo-hydrazone isomerization proceeds much faster than the attack of singlet oxygen on the hydrazone form, which explains all observed facts.