233-59-0

Basic information

• Product Name: 2H-naphtho[1,2-d][1,2,3]triazole
• Synonyms: 3H-naphtho[1,2-d]-1,2,3-triazole
• CAS NO: 233-59-0
• Molecular Formula: C₁₀H₇N₃
• Molecular Weight: 169.1827
• Mol File: 233-59-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 392.8°C at 760 mmHg
• Flash Point: 193.2°C
• Density: 1.381g/cm³
• Vapor Pressure: 2.23E-06mmHg at 25°C
• Refractive Index: 1.804
• CAS DataBase Reference: 2H-naphtho[1,2-d][1,2,3]triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-naphtho[1,2-d][1,2,3]triazole(233-59-0)
• EPA Substance Registry System: 2H-naphtho[1,2-d][1,2,3]triazole(233-59-0)

Safety Data

• Hazardous Substances Data: 233-59-0(Hazardous Substances Data)

Usage

Description

2H-naphtho[1,2-d][1,2,3]triazole, also known as Naphthalen-2-yl-[1,2,3]triazole, is a heterocyclic compound characterized by a naphthalene ring fused to a triazole ring. It is widely recognized in the field of organic chemistry for its role as a building block in the synthesis of new organic compounds with potential biological activities. This chemical is noted for its high stability and has been a subject of interest in materials science for its potential use in organic semiconductors and optoelectronic devices. Furthermore, research has indicated that derivatives of 2H-naphtho[1,2-d][1,2,3]triazole may possess anti-cancer and anti-microbial properties.

Uses

Used in Organic Chemistry:
2H-naphtho[1,2-d][1,2,3]triazole is used as a building block for synthesizing new organic compounds with potential biological activities, due to its unique structure and stability.
Used in Materials Science:
In the field of materials science, 2H-naphtho[1,2-d][1,2,3]triazole is utilized in the development of organic semiconductors and optoelectronic devices, capitalizing on its stability and electronic properties.
Used in Pharmaceutical Research:
2H-naphtho[1,2-d][1,2,3]triazole derivatives are studied for their potential as anti-cancer and anti-microbial agents, showing promise in various research studies for their therapeutic applications.

Upstream product

• 82424-48-4 2-acetylamino-1-naphthylamine 
• 938-25-0 1,2-diaminonaphthalene 
• 606-57-5 1-nitro-2-naphthylamine 
• 111180-88-2 1-azido-2-bromonaphthalene 
• 771-14-2 2-bromonaphthalen-1-amine 
• 134-32-7 1-amino-naphthalene 
• 252054-88-9 1-(trimethylsilyl)naphthalen-2-yl triflate 

Relevant articles and documents

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

Compounds and methods

Compounds of this invention are non-peptide, reversible inhibitors of type 2 methionine aminopeptidase, useful in treating conditions mediated by angiogenesis, such as cancer, haemangioma, proliferative retinophathy, rheumatoid arthritis, atherosclerotic