83-53-4

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Dibromonaphthalene is used as a pharmaceutical intermediate for the synthesis of novel, orally active dual NK1/NK2 antagonists. These antagonists have potential applications in treating various conditions, such as anxiety, depression, and other disorders related to the neurokinin receptor system.
Used in Chemical Synthesis:
1,4-Dibromonaphthalene is used as a starting material for the synthesis of tribromo methoxynaphthalenes, which are compounds with potential applications in various chemical and industrial processes.
Additionally, 1,4-dibromonaphthalene is used in the preparation of 5,8-dibromo-1,4-naphthoquinone and 5,8-diiodo-1,4-naphthoquinone, which are important intermediates in the synthesis of various organic compounds and may have potential applications in the development of new pharmaceuticals and other chemical products.
Used in Annelation of PAHs:
1,4-Dibromonaphthalene is also used in the annelation of polycyclic aromatic hydrocarbons (PAHs), which are a class of compounds with potential applications in various fields, such as materials science, organic synthesis, and pharmaceuticals. The annelation process involves the formation of additional rings in the PAH structure, leading to the creation of more complex and functionalized molecules.

Preparation

An environment-friendly method was developed to synthesize 1,4-dibromonaphthalene (1,4-DBN) using 1,3-dialkylimidazolium and pyridinium ionic liquids as catalysts, over which the yields of 1,4-DBN were obtained as high as 100%.An environment-friendly method for synthesis of 1,4-dibromo-naphthalene in aqueous solution of ionic liquids

InChI:InChI=1/C10H6Br2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

Upstream product

• 91-20-3 naphthalene 
• 119-64-2 tetralin 
• 90-11-9 1-Bromonaphthalene 
• 4236-05-9 4-bromo-1-nitronaphthalene 
• 2298-07-9 4-Bromo-1-naphthylamine 
• 116632-13-4 1,4-dibromonaphthalen-2-amine 
• 19922-78-2 1,2,3,4-tetrabromo-1,2,3,4-tetrahydronaphthalene 
• 91-17-8 decalin 
• 7726-95-6 bromine 
• 67-66-3 chloroform 
• 110-46-3 isopentyl nitrite 
• 85-47-2 1-naphthalenesulfonic acid 
• 7789-69-7 phosphorus pentabromide 
• 7732-18-5 water 

Downstream Products

• 24157-79-7 1,4-diisopropylnaphthalene 
• 571-58-4 1,4-dimethylnaphthalene 
• 1024-47-1 1,4-Bis(trimethylsilyl)naphthalin 
• 91-20-3 naphthalene 
• 90-11-9 1-Bromonaphthalene 
• 13720-06-4 2,6-dibromonaphthalene 
• 16650-55-8 4-bromonaphthalene-1-carboxylic acid 
• 36316-83-3 1,4-diiodonaphthalene 
• 22871-75-6 naphthalene-1,4-diyldiboronic acid 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 92616-49-4 4-bromonaphthalene-1-carbonitrile 
• 206-44-0 fluoranthene 
• 193-43-1 indeno[123-cd]fluoranthene 
• 863090-19-1 N,N'-bis(p-bromonaphthalen-1-yl)-N,N'-diphenylbiphenyl-4,4'-diamine 

Relevant academic research and scientific papers

Oxygen-Doped PAH Electrochromes: Difurano, Dipyrano, and Furano-Pyrano Containing Naphthalene-Cored Molecules

In this work, we report the synthesis of O-doped naphthalene-based electrochromes. Exploiting the CuO-mediated Pummerer oxidative cycloetherification reaction, a series of 1,4- and 1,5-disubstituted naphthalene-cored dipyrano, difurano, and furano-pyrano polycyclic aromatic hydrocarbons (PAHs) have been prepared. Steady-state UV-Vis absorption and emission investigations showed that the spectroscopic profile strongly depends on the O-doping topology, with the dipyrano and the difurano derivatives demonstrating the most red-shifted and blue-shifted electronic transition, respectively. Computational investigations revealed that the cycloetherification reaction raises the HOMO energy level (while the LUMO remains largely unaffected), with the dipyrano derivatives displaying the highest values. Spectroelectrochemical measurements showed that, depending on the O-topology and the type of O-ring, different electrochromic responses could be obtained with colour transitions featuring high contrasts involving yellow, pink, orange or blue colours.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Preparation method of high-purity 1,4-dibromonaphthalene

The invention relates to a preparation method of high-purity 1,4-dibromonaphthalene and belongs to the technical field of organic synthesis. The provided preparation method of high-purity 1,4-dibromonaphthalene aims to solve the problems that preparation methods of 1,4-dibromonaphthalene in the prior art are complicated, the reaction conditions are high, the product purity is low, the yield is low, and the product quality is unstable. The method comprises the four steps of a one-pot acetylation protection and selective bromination process, a hydrolysis deprotection process, a diazotization coupling reaction process and a recrystallization purification process to obtain high-purity 1,4-dibromonaphthalene. The provided preparation method has the advantages that the synthesis route is short,the reaction conditions are mild and easy to control, and the production cost is low. The organic synthesis reaction site is monotonous, the selectivity is high, the product purity is up to 99.0%, andthe total yield can reach 71.7%. Industrial production is easily realized, the need for large-scale production of 1,4-dibromonaphthalene can be effectively met, and the method has a broad applicationprospect.

PROCESS FOR PRODUCING 1,5-DIBROMONAPHTHALENE

PROBLEM TO BE SOLVED: To provide a process for producing 1,5-dibromonaphthalene that can efficiently produce 1,5-dibromonaphthalene. SOLUTION: 1,5-dibromonaphthalene is produced by a process for producing 1,5-dibromonaphthalene having a bromination step of reacting at least one of naphthalene and 1-bromonaphthalene with bromine in the presence of a porous material. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Composite taken as URAT 1 inhibitor

The invention provides a series of composite with a formula (I), wherein n is selected from 1, 2 or 3, X is selected from O or S, Q is selected from C or N, and R is selected from H, halogen or -C1-6.The composite can be used as the URAT 1 inhibitor and can be used for treating hyperuricemia and gout.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Fluorescence properties of 1-(silylethynyl)naphthalenes and 1,4-bis(silylethynyl)naphthalenes in solutions, thin films and solid states

1-(Silylethynyl)naphthalenes (1a-e) and 1,4-bis(silylethynyl)naphthalenes (2a-c) were prepared, and their fluorescence properties were evaluated in solutions, thin films and solid states. In dilute solutions, monomer emission is observed from substances in both groups and the relative fluorescence quantum yields of 1a-e increase as the steric bulk of the substituents on silicon increase. The observed concentration dependence of fluorescence intensities indicates that the self-quenching has a more pronounced effect on emission in shorter wavelength regions than that in longer wavelength regions. Analysis of Stern–Volmer type plots shows that formation of both an excimer and a termolecular excited complex is involved in fluorescence quenching of 1 in solution, whereas only an excimer is involved in quenching of 2. Fluorescence in thin films and solid states dispersion in KBr is dependent on number of silylethynyl groups present in the naphthalene derivatives. For example, excimer emission occurs from 1 while monomer emission occurs mainly from 2. X-ray crystallographic analysis of the crystal packing structure shows that 2b would have difficulty with forming an excimer because of steric hindrance, but that 2a can partially form an excimer owing to the slipped head-to-tail parallel orientation of naphthalene rings on neighboring molecules. The results of this effort demonstrate that the emission properties of 1- and 1,4-bis(silylethynyl)naphthalenes are influenced by the number of silylethynyl groups, the steric bulk of substituents on silicon atoms, and the compound's present state.

Polybrominated methoxy- and hydroxynaphthalenes

Regio- and stereoselective synthesis are described for convenient preparation of hydroxy- and methoxynaphthalenes starting from naphthalene (1). cis,cis,trans-2,3,5,8-Tetrabromo-4-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (6), cis,cis,trans-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (7), and cis,cis,cis-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (8) were obtained with silver-induced substitution of trans,cis,trans-1,2,3,4, 5,8-hexabromo-1,2,3,4-tetrahydronaphthalene (3). Base-promoted aromatization of dimethoxides 7 and 8 afforded 3,5,8-tribromo-1-methoxynaphthalene (9) and 2,5,8-tribromo-1-methoxynaphthalene (10). The reaction of 6 with sodium methoxide formed compounds 10 and 3,5,8-tribromonaphthalen-1-ol (16). Bromination of 9 and 16 with Br2 in dichloromethane at room temperature produced 2,3,5,8-tetrabromo-1-methoxynaphthalene (14) and 2,3,4,5,8-pentabromonaphthalen-1-ol (18), respectively, while compound 10 did not react in the same conditions. Pyridine-induced elimination of hexabromide 3 afforded 1,4,6-tribromnaphthalene (21) in 99% yield and thermolysis of the hexabromide 3 gave mainly 1,4,6,7-tetrabromonaphthalene (22). Tetrabromide 22 was transformed to 1,4,6,7-tetramethoxynaphthalene (23) by copper-assisted nucleophilic substitution reaction.

WAVELENGTH CONVERSION MATERIAL FOR HIGHLY EFFICIENT DYE-SENSITIZED SOLAR CELL, AND PREPARATION METHOD THEREOF

Novel compounds represented by the present invention refers to formula 1 or formula 2, said novel compounds including wavelength change material, and including said wavelength change material relates to dye-sensitized solar cell.

PYRABACTIN ANALOGUES TO MODULATE PLANT DEVELOPMENT

The present invention relates to compounds which can be used to control plant development. Indeed, the present invention discloses a new class of pyrabactin analogues which have a physiological effect on -for example- seed germination, and/or stomatal closure, and/or have developmental effects on root and shoot development and organogenesis. Hence, the latter compounds can be used to control plant development such as -for example- increasing the tolerance of plants to drought stress or to control physiological phenomena such as pre-harvest sprouting, tolerance to pathogens etc.