76599-37-6

Basic information

• Product Name: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole
• Synonyms: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole
• CAS NO: 76599-37-6
• Molecular Weight: 279.385
• Mol File: 76599-37-6.mol

Chemical Properties

• CAS DataBase Reference: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole(76599-37-6)
• EPA Substance Registry System: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole(76599-37-6)

Safety Data

• Hazardous Substances Data: 76599-37-6(Hazardous Substances Data)

Upstream product

• 24886-73-5 1-Azidoadamantane 
• 536-74-3 phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 768-90-1 1-Adamantyl bromide 
• 102-96-5 (2-nitroethenyl)benzene 

Relevant articles and documents

Synthesis of adamantyl substituted 1,2,3-triazol-5-ylidene ligands and their PEPPSI-type palladium complexes

PEPPSI-type Pd-complexes with the bulky mesoionic 1,2,3-triazolium carbenes (tzNHC) substituted by the adamantyl groups were prepared from 1-azidoadamantane and 1-ethynyladamantane. The X-ray analysis revealed that 1,4-diadamantyl-tzNHC complex (TAd-PEPPSI) showed longer Pd-C bond length than 1-adamantyl-4-phenyl-tzNHC complex (TAdPh-PEPPSI) and 1,4-diphenyl-tzNHC complex (TPh-PEPPSI). These complexes were applied to Hiyama coupling reaction between aryl bromides and phenyltrimethoxysilane. TAd-PEPPSI rapidly initiates the reaction, and TAdPh-PEPPSI gave good product yields.

Carbene transfer from triazolylidene gold complexes as a potent strategy for inducing high catalytic activity

A series of gold(I) complexes [AuCl(trz)] were synthesized that contain 1,2,3-triazolylidene (trz) ligands with variable wingtip groups. In the presence of AgBF4, these complexes undergo ligand redistribution to yield cationic complexes [Au(trz)2]BF4 in high yields as a result of efficient carbene transfer. Identical reactivity patterns were detected for carbene gold complexes comprised of Arduengo-type IMes ligands (IMes = N,N′-dimesityl-imidazol-2-ylidene). Reaction of cationic complexes [Au(trz)2]+ with [AuCl(trz′)] afforded the heteroleptic complex [Au(trz)(trz′)]+ and [AuCl(trz)] (trz, trz′ = triazolylidene ligands with different wingtip groups). Carbene transfer occurs spontaneously, yet is markeldy rate-enhanced in the presence of Ag+. The facile carbene transfer was exploited as a catalyst activation process to form active gold species for the aldol condensation of isocyanides and aldehydes to form oxazolines. The catalytic activity is strongly dependent on the presence of Ag+ ions to initiate catalyst activation. High turnovers (105) and turnover frequencies (10 4 h-1) were accomplished. Structural analysis at early stages of the reaction support the critical role of triazolylidene dissociation to activate the precatalyst and dynamic light scattering revealed the presence of nanoparticles (±100 nm diameter) as potential catalytically active species. Furthermore, the triazolylidene scaffold had no impact on the diastereoselectivity of the oxazoline formation, and chiral triazolylidenes did not induce any asymmetry in the product. The facile dissociation of carbenes from [AuCl(carbene)] in the presence of Ag+ ions suggests a less stable Au-Ccarbene interaction than often assumed, with potential implications for gold-catalyzed reactions that employ a silver salt as (putative) halide scavenger.

Assembly of four modules onto a tetraazide platform by consecutive 1,2,3-triazole formations

Efficient consecutive 1,2,3-triazole formations using multiazide platforms are disclosed. On the basis of unique clickability of the 1-adamantyl azido group, a four-step synthesis of tetrakis(triazole)s was achieved from a tetraazide platform molecule. This method was applied to a convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.

Influence of steric demand on ruthenium-catalyzed cycloaddition of sterically hindered azides

The RuAAC of sterically hindered 2,2-diaryl-2-azidoamines and terminal alkynes resulted in the unprecedented formation of 1,4-disubstituted-1,2,3-triazoles. A control experiment with 2-(azidomethyl)pyrrolidine revealed the usual selectivity with RuAAC and

Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water

Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.

COMPOUNDS WHICH HAVE A PROTECTIVE ACTIVITY WITH RESPECT TO THE ACTION OF TOXINS AND OF VIRUSES WITH AN INTRACELLULAR MODE OF ACTION

The subject matter of the present invention is novel families of compounds which are aromatic amine, imine, aminoadamantane and benzodiazepine derivatives, medicaments comprising same and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as, for example, ricin, and of viruses that use the internalization pathway for infecting cells.

Polystyrene resin-supported CuI-cryptand 22 complex: A highly efficient and reusable catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles under aerobic conditions in water

Polystyrene resin-supported copper(I) iodide-cryptand-22 complex (PS-C22-CuI) was synthesized and characterized by FT-IR, EDX, SEM, XPS, and TG-DTA analysis. This complex was found to be a highly active and robust heterogeneous catalyst for either three-component reaction of organic halides, sodium azide, and terminal alkynes, or the reaction of organic azides and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good to excellent yields at room temperature, using water as the green solvent. The catalyst can be not only easily isolated from the final product by filtration but also reused without significant loss of catalytic activity.

Copper on iron: Catalyst and scavenger for azide-alkyne cycloaddition

Dipolar cycloaddition of terminal alkynes and azides catalyzed by the Cu/Fe bimetallic system is reported. In the presence of a readily accessible nanosized copper source, the cycloaddition reaction can be easily achieved at ambient temperature with high

Stabilization of Cu(0)-nanoparticles into the nanopores of modified montmorillonite: An implication on the catalytic approach for "click" reaction between azides and terminal alkynes

In situ generation of Cu(0)-nanoparticles in the nanopores of modified montmorillonite and their catalytic activity in 1,3-dipolar cycloaddition reactions between azides and terminal alkynes to synthesise 1,2,3-triazoles have been carried out. The modific

Fast, ligand- and solvent-free copper-catalyzed click reactions in a ball mill

A new, ligand- and solvent-free method for the Huisgen 1,3-dipolar cycloaddition (click reaction) was developed using a planetary ball mill. Besides various alkynes and azides, a propargyl functionalized polymer was converted by mill clicking. Moreover, it was possible to carry out a click polymerization in a ball mill.