91165-90-1

Basic information

• Product Name: 1-(1-Naphtyl)-1H-1,2,3-triazole-4-carboxylic acid ethyl ester
• Synonyms: 1-(1-Naphtyl)-1H-1,2,3-triazole-4-carboxylic acid ethyl ester
• CAS NO: 91165-90-1
• Molecular Weight: 0
• Mol File: 91165-90-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(1-Naphtyl)-1H-1,2,3-triazole-4-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-Naphtyl)-1H-1,2,3-triazole-4-carboxylic acid ethyl ester(91165-90-1)
• EPA Substance Registry System: 1-(1-Naphtyl)-1H-1,2,3-triazole-4-carboxylic acid ethyl ester(91165-90-1)

Safety Data

• Hazardous Substances Data: 91165-90-1(Hazardous Substances Data)

Upstream product

• 6921-40-0 1-azidonaphthalene 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 91165-89-8 methyl 1-(1-naphthyl)-1,2,3-triazole-4-carboxylate 
• 113423-89-5 1-(1-naphthyl)-1H-1,2,3-triazole-4-carboxylic acid 
• 81945-58-6 1-(1'H-1',2',3'-triazolyl)naphthalene 

Relevant articles and documents

Photolysis of 1-Aryl-1,2,3-triazoles; Rearrangement via !H-Azirines

The preparation and photolysis of a series of 1-(1-naphthyl)-1,2,3-triazoles, (2)-(5), and of 1-(2-methyl-1-naphthyl)-1,2,3-triazoles, (6)-(9), with and without electron-withdrawing groups (CO2R, CONH2, CN, CHO, COPh) in the triazole ring, are described.In the first series, triazoles (3) with two electron-withdrawing groups, and triazoles (4) with one such group at C-4, mostly give good yields of the expected benzindoles (10) and 11 respectively.Triazoles (5) with the electron-withdrawing group at C-5 also give benzindoles but these are now mixtures of the expected (12) and rearranged indoles (11).Photolysis of the 1-phenyltriazoles (21) and (22) follows the same pattern, those with the electron-withdrawing group at C-5 rearranging to give mixtures of indoles (23) and (24).This is explained by a mechanism (Scheme 3) in which the less stable carbene intermediate (13) rearranges to the more stable carbene (15) via the 1H-azirine (14), in competition with its direct cyclisation.This provides the first evidence for antiaromatic 1H-azirines as intermediates in a photochemical reaction.Photolysis of the 2-methylnaphthyl compounds follows a different path: diester (7b) and dinitrile (7d) give high yields of the deeply coloured 9-methyl-1H-benzoquinoline derivatives (25a) and (25b) respectively, the first stable examples of this ring system to be isolated.Photolysis of the nitrile (8c) gives 9b-methyl-9bH-benzindole-3-carbonitrile (28), a rare example of a stable indole with a ring junction substituent. 1,2-Shifts in the carbenes are only observed with the bis(trimethylsilyl)triazoles (2d) and (6f), in keeping with the known rapid migration of trimethylsilyl groups to carbene centres.

Syntheses and Spectroscopic Studies of 1,8-Bistriazolylnaphthalenes

The first 1,8-diheterocyclic naphthalenes, the 1,8-bis(1'H-1',2',3'-triazolyl)naphthalenes (1a - i), have been synthesized by 1,3-dipolar cycloadditions of 1,8-diazidonaphthalene to acetylenic esters or enolates of acetoacetic esters, and have strained structures as revealed by comparison of their spectral properties with those of the corresponding 1-(1'H-1',2',3'-triazolyl)naphthalenes.