21665-69-0

Basic information

• Product Name: 2H-Naphtho[1,2-d]triazole, 2-phenyl-
• CAS NO: 21665-69-0
• Molecular Formula: C16H11N3
• Molecular Weight: 245.283
• Mol File: 21665-69-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2H-Naphtho[1,2-d]triazole, 2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Naphtho[1,2-d]triazole, 2-phenyl-(21665-69-0)
• EPA Substance Registry System: 2H-Naphtho[1,2-d]triazole, 2-phenyl-(21665-69-0)

Safety Data

• Hazardous Substances Data: 21665-69-0(Hazardous Substances Data)

Upstream product

• 47487-14-9 1-(Phenylazo)-N-benzylidene-2-naphthylamine 
• 7647-01-0 hydrogenchloride 
• 67764-33-4 cyclopentyl nitrite 
• 64-19-7 acetic acid 
• 96627-67-7 (E)-1-(phenyldiazenyl)naphthalen-2-amine 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 91-59-8 naphthalen-2-ylamine 
• 83210-06-4 {Cu(C₆H₅NNC₁₀H₆(NH))2} 
• 100-34-5 benzene diazonium chloride 
• 56-23-5 tetrachloromethane 
• 85-84-7 1-phenylazo-2-naphthylamine 
• 7722-84-1 dihydrogen peroxide 
• 98-95-3 nitrobenzene 
• 7719-09-7 thionyl chloride 

Downstream Products

• 122510-89-8 4-hydroxyimino-5-oxo-2-phenyl-2H-naphtho<1,2-d>triazole 
• 122510-85-4 5-(2-carboxyphneyl)-2-phenyl-4-carboxy-2H-1,2,3-triazole 
• 37155-63-8 2-phenyl-2H-naphtho[1,2-d][1,2,3]triazole-4,5-dione 

Relevant articles and documents

Copper-Catalyzed Cyclization of Aryl Amines and Aryldiazonium Salts under Air: Access to N-2-Aryl-Naphthotriazoles

A catalytic and step economic protocol for the construction of N-2-aryl-naphthotriazoles via copper-catalyzed cyclization of aryl amines and aryldiazonium salts is reported. With dioxygen in the air as termial oxidants under copper catalysis, various N-2-aryl-naphthotriazoles were synthesized in high yields. Importantly, this protocol features the sufficient inhibition of the classic C-N2 bond cleavage process of aryldiazonium tetrafluoroborates under copper catalysis and the undesired dehydrogenative coupling of aryl amines under oxidative conditions. Preliminary mechanistic studies indicated that a radical procedure might not be involved in this transformation. In addition, simple decoration of the obtained compounds delivers novel and attractive tetraphenylethylene moiety containing N-2-aryl-naphthotriazole derivatives. (Figure presented.).

A Simple Route to 2H-Naphtho1,2,3-triazoles

1-Arylazo-2-chloro-naphthalenes 9a-9k and 2,4-diarylazo-1-chloronaphthalenes 10a-10c are transformed by the reaction with sodium azide into 2-arylsubstituted 2H-Naphtho1,2,3-triazoles 13a-13k and 14a-14c, resp., which exhibit fluorescence if they a

Oxidative Cyclizations. VII. Cyclization of 2-Substituted Anilines with Alkaline Hypohalite

The Green-Rowe oxidation of 2-nitroanilines with alkaline hypohlorite, to yield benzofuroxans, is demonstrated by studies of the visible spectra of transient intermediates to proceed through N-chlorination and a singlet nitrene.Two variations on the route to the nitrene are possible.The cyclization step is represented as an internal capture of the nitrene by the ortho substituent, and on this basis the Green-Rowe oxidative cyclization is now extended to anilines whose ortho substituent is benzoyl or phenylazo.It is not however successful for ortho phenyl.Azo compounds were observed as byproducts in some of these reactions, and are shown to arise via N,N-dichloroanilines.