67291-63-8

Basic information

• Product Name: 2-Amino-3-methoxynaphthalene
• Synonyms: 2-Amino-3-methoxynaphthalene;3-Methoxy-naphthalen-2-ylamine
• CAS NO: 67291-63-8
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21114
• Mol File: 67291-63-8.mol

Chemical Properties

• Melting Point: 107 °C
• Boiling Point: 333.2°C at 760 mmHg
• Flash Point: 170.9°C
• Appearance: /
• Density: 1.156g/cm³
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.655
• PKA: 4.08±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-3-methoxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-methoxynaphthalene(67291-63-8)
• EPA Substance Registry System: 2-Amino-3-methoxynaphthalene(67291-63-8)

Safety Data

• Hazardous Substances Data: 67291-63-8(Hazardous Substances Data)

Usage

Uses

Used in Fluorescent Dye Applications:
2-Amino-3-methoxynaphthalene is used as a fluorescent dye for labeling and detection of proteins and nucleic acids. It absorbs light at a wavelength of around 318 nanometers and emits fluorescence at approximately 390 nanometers, making it suitable for use in fluorescence microscopy and flow cytometry.
Used in Organic Synthesis:
2-Amino-3-methoxynaphthalene is used as an intermediate in the production of pharmaceuticals and other fine chemicals. Its unique chemical structure allows for various chemical reactions and modifications, contributing to the synthesis of a wide range of organic compounds.
Used in Research and Development:
2-Amino-3-methoxynaphthalene is used in research and development for studying the properties and behavior of aromatic compounds, as well as for developing new applications and techniques in fluorescence microscopy, flow cytometry, and other related fields.
It is important to handle 2-Amino-3-methoxynaphthalene with care, as prolonged exposure or ingestion can lead to various health hazards.

InChI:InChI=1/C11H11NO/c1-13-11-7-9-5-3-2-4-8(9)6-10(11)12/h2-7H,12H2,1H3

Upstream product

• 91137-51-8 3-nitro-2-naphthyl methyl ether 
• 13042-06-3 3-methoxy-[2]naphthoic acid amide 
• 412036-46-5 (3-methoxy-[2]naphthyl)-carbamic acid ethyl ester 
• 32361-60-7 3-nitro-naphthalen-2-ol 
• 100192-99-2 3-nitro-5,6,7,8-tetrahydro-2-naphthyl acetate 
• 883-62-5 3-methoxy-2-naphthoic acid 
• 58778-69-1 3-methoxy-2-naphthoyl chloride 
• 58698-35-4 3-methoxy-2-naphthoic hydrazide 
• 1433906-99-0 tert-butyl (3-methoxynaphthalen-2-yl)carbamate 
• 1044506-37-7 tert-butyl(3-hydroxynaphthalen-2-yl)carbamate 
• 5417-63-0 3-Amino-2-naphthol 
• 93-04-9 2-Methoxynaphthalene 
• 13041-60-6 methyl 3-methoxy-2-naphthoate 
• 228401-15-8 2-(N-(carbobenzyloxy)amino)-3-methoxynaphthalene 

Downstream Products

• 795278-91-0 3-iodo-2-methoxynaphthalene 
• 2037-17-4 2-methoxy-3-phenylazo-naphthalene 
• 90073-02-2 (Z)-ethyl phenylpyruvate 2-<(3-methoxy-2-naphthyl)hydrazone> 
• 90073-03-3 (E)-ethyl phenylpyruvate 2-<(3-methoxy-2-naphthyl)hydrazone> 
• 284462-37-9 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide 
• 1572936-82-3 N-((3-methoxy)-2-naphthyl)-5-nitroanthranilic acid 
• 30478-88-7 3-bromo-2-naphthol 

Relevant articles and documents

Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling

A challenging direct asymmetric catalytic aerobic oxidative cross-coupling of 2-naphthylamine and 2-naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′-disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H-1,8 of 2-naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross-coupling reaction.

Transition-metal-free access to primary anilines from boronic acids and a common +NH2 equivalent

Diversely substituted anilines are prepared by treatment of functionalized arylboronic acids with a common, inexpensive source of electrophilic nitrogen (H2N-OSO3H, HSA) under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method. However, even moderately electron-poor substrates are well tolerated under the room temperature conditions. Sterically hindered substrates appear to be equally effective compared to unhindered ones. Highly electron-deficient substrates afford product in very low yields at room temperature, but moderate to good yields are obtained at refluxing temperatures. Our method is also amenable to electrophilic amination of several common boronic acid derivatives (e.g., pinacol esters). We demonstrate that it can be combined with metal-halogen exchange reactions or a variety of directed ortho metalation protocols in a "one-pot" sequence for the synthesis of aromatic amines with unique substitution patterns. DFT studies, in combination with experimental results, suggest that the reaction occurs via base-mediated activation of HSA, followed by 1,2 aryl B-N migration. This mode of activation appears to be critical for the success of the reaction and allows, for the first time, a general, electrophilic amination of boronic acids at ambient temperature.

Organocatalytic aryl-aryl bond formation: An atroposelective [3,3]-rearrangement approach to BINAM derivatives

Herein we disclose an organocatalytic aryl-aryl bond-forming process for the regio- and atroposelective synthesis of 2,2′-diamino-1,1′- binaphthalenes (BINAMs). In the presence of catalytic amounts of axially chiral phosphoric acids, achiral N,N′-binaphthyl hydrazines undergo a facile [3,3]-sigmatropic rearrangement to afford enantiomerically enriched BINAM derivatives in good to excellent yield. This transformation represents the first example of a metal-free, catalytic C(sp2)-C(sp2) bond formation between two aromatic rings with concomitant de novo atroposelective installation of an axis of chirality. Density functional calculations reveal that, in the transition state for C-C bond formation, the phosphoric acid proton of the catalyst is fully transferred to one of the N-atoms of the substrate, and the resulting phosphate acts as a chiral counterion.

Monna, a potent and selective blocker for transmembrane protein with unknown function 16/anoctamin-1

Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established (Oh et al., 2008). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a-NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC 5050 of 0.08 μM for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10～30 μM MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia.

Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas

This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS

This invention relates to the use of a group of aryl ureas in treating cytokine mediated diseases and proteolytic enzyme mediated diseases, and pharmaceutical compositions for use in such therapy.

Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas

This invention relates to the use of a group of aryl ureas in treating cytokine mediated diseases and proteolytic enzyme mediated diseases, and pharmaceutical compositions for use in such therapy.

Inhibition of raf kinase using symmetrical and unsymmetrical substituted diphenyl ureas

This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors

This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors

This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.