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Usage

Uses

Used in Chemical Synthesis:
2,6-Dimethoxynaphthalene is used as an intermediate in the synthesis of various organic compounds and dyes. Its unique structure allows for the creation of a wide range of derivatives with diverse applications in the chemical industry.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,6-Dimethoxynaphthalene is studied for its potential antifungal and antimicrobial properties. Its ability to inhibit the growth of certain fungi and bacteria makes it a candidate for the development of new antimicrobial agents.
Used in Material Science:
2,6-Dimethoxynaphthalene is utilized in the development of optical and electronic materials due to its light-absorbing and fluorescent characteristics. These properties are beneficial for applications in areas such as sensors, displays, and photovoltaic devices.
Used in Research:
In the field of scientific research, 2,6-Dimethoxynaphthalene serves as a model compound for studying the effects of methoxy substitution on the physical and chemical properties of naphthalene derivatives. This helps in understanding the structure-property relationships and contributes to the advancement of material science and organic chemistry.

InChI:InChI=1/C17H10N2O2/c20-16-13-7-1-4-11-5-2-8-14(15(11)13)17(21)19(16)12-6-3-9-18-10-12/h1-10H

Upstream product

• 67-56-1 methanol 
• 581-43-1 2.6-dihydroxynaphthalene 
• 80-48-8 methyl p-toluene sulfonate 
• 74-83-9 methyl bromide 
• 5111-66-0 6-Methoxy-2-naphthol 
• 75-57-0 tetramethlyammonium chloride 
• 135-76-2 sodium 2-naphthol-6-sulfonate 
• 613-20-7 2,6-naphthoquinone 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 582-17-2 2,7-Dihydroxynaphthalene 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 649724-98-1 (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone 
• 1621149-48-1 C₂₉H₃₂O₅ 
• 25315-11-1 2,6-Dimethoxy-1-iod-naphthalin 
• 25315-10-0 1-bromo-2,6-dimethoxynaphthalene 

Relevant academic research and scientific papers

SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX

Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.

A novel methoxy-decorated metal-organic framework exhibiting high acetylene and carbon dioxide storage capacities

A methoxy-decorated novel metal-organic framework (MOF), Cu2(DTPD) (ZJU-12, H4DTPD = 5,5′-(2,6-dimethoxynaphthalene-1,5-diyl)diisophthalic acid) with optimized pore space and open metal sites, was solvothermally synthesized and structurally characterized. The activated ZJU-12a displays a moderately high BET (Brunauer-Emmett-Teller) surface area of 2316 m2 g?1. Due to the pore size of the crystal being consistent with the molecular size and kinetic diameters of C2H2 and CO2, ZJU-12a exhibits a high C2H2 storage capacity of 244 cm3 g?1 and CO2 capture capacity of 134 cm3 g?1 at room temperature.

A New Microporous Metal-Organic Framework for Highly Selective C2H2/CH4 and C2H2/CO2 Separation at Room Temperature

We have successfully designed and synthesized a new tetracarboxylic linker, which constructed its first three-dimensional microporous metal-organic framework (MOF), [Cu2(DDPD)(H2O)2]?Gx (ZJU-13, H4DDPD=5,5'-(2,6-dihydroxynaphthalene-1,5-diyl)diisophthalic acid, ZJU=Zhejiang University, G = guest molecules) via solvothermal reaction. Due to open Cu2+ sites and optimized pore size, the activated ZJU-13a displays high separation selectivity for C2H2/CH4 of 74 and C2H2/CO2 of 12.5 at low pressure by using Ideal Adsorbed Solution Theory (IAST) simulation at room temperature.

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.

1:1 and 2:1 cocrystallizations of alkoxy-substituted naphthalene derivatives with octafluoronaphthalene through arene-perfluoroarene interactions

Naphthalene derivatives with laterally orientated short side chains readily form cocrystals with octafluoronaphthalene in which the position and the length of the lateral chain can control the 1:1 and 2:1 cocrystallization stoichiometries and overlapped a

New alkoxy-functionalized naphthodithiophene-based semiconducting oligomers and polymers

We report the syntheses and characterization of two bent dialkoxy-substituted naphthodithiophene (bNDT) isomers as well as of the corresponding bNDT-based small molecule and polymer semiconductors for organic field-effect transistors and organic photovoltaics. The bNDT-based building blocks exhibit improved oxidation potential and photo- and air stability versus the benzodithiophene and linear naphthodithiophene counterparts. Incorporation of the dialkoxy substituents enables film fabrication from solution and control of the molecular solid-state packing. Among these semiconductors, the polymer P1 exhibits good hole field-effect mobility of about 0.4 cm2 Vs -1 with Ion/Ioff>104 for low-temperature annealing. These results indicate that bNDT is a promising building block for optoelectronic semiconducting materials.

A convenient and efficient synthesis of 2,6-dihydroxynaphthalene

A convenient synthesis of 2,6-dihydroxynaphthalene from 6-bromo-2-naphthol has been achieved with high overall yield (52%) and good purity (95.7%) based on the conversion of 6-(methoxymethoxy)-2-naphthaldehyde to 6- (methoxymethoxy)-2-naphthol formate by a Baeyer-Villiger oxidation- rearrangement. Compared with the reported methods, the reaction conditions are milder and the work-up of each step is much simpler. Moreover, 6-bromo-2-naphthol as the starting material for the synthesis is readily available.

Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen- 2-one as a new class of microtubule-targeting agents

A series of 1-benzylidene-3,4-dihydronaphthalen-2-one derivatives were designed and synthesized, and their biological activities in vitro and in vivo were evaluated. The results showed a number of the title compounds exhibiting potent nanomolar activity in several human cancer cell lines. Of these, compound 22b showed the strongest inhibitory activity against human CEM, MDA-MBA-435, and K562 cells (IC50 = 1 nM), displayed in vitro inhibition of tubulin polymerization (IC50 = 3.93 μM), and significantly induced cell cycle arrest in G2/M phase. In addition, compound 22b could inhibit the tumor growth in colon nude mouse xenograft tumor model significantly and seemed safer than CA-4 when achieving a similar tumor suppression. This study provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

Microwave-assisted methylation of phenols with tetramethylammonium chloride in the presence of K2CO3 or Cs2CO3

We have evaluated the potential of using tetramethylammonium chloride (Me4NCl) as an alternative methylating agent for phenols under microwave-assisted conditions. Its chemical behavior was tested in a reaction with 2-naphthol in the presence of various bases and solvents. The method was then applied in 1,2-dimethoxyethane or toluene under heterogeneous conditions for the O-methylation of a series of phenolic compounds. We found that many simple phenols can be methylated in the presence of K2CO3, whereas some other less-reactive phenols require the presence of the more reactive Cs2CO3.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.