51118-27-5

Usage

Chemical structure

A triazole derivative with a phenylmethyl group and a phenyl group attached to the 5-position of the triazole ring

Potential applications

Building block for the synthesis of pharmaceuticals, agrochemicals, and materials, development of coordination polymers and metal-organic frameworks

Importance

Valuable intermediate in organic synthesis, promising candidate for further research in drug discovery and material science.

Upstream product

• 108842-69-9 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid 
• 536-74-3 phenylacetylene 
• 622-79-7 benzyl azide 
• 637-44-5 phenylpropyolic acid 
• 4368-68-7 1-benzyl-1H-[1,2,3]triazole 
• 108-86-1 bromobenzene 
• 100-39-0 benzyl bromide 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 100-44-7 benzyl chloride 
• 1422251-36-2 3-benzyl-1-(3,4-dimethoxybenzyl)-4-phenyl-1H-1,2,3-triazolium bromide 
• 766-97-2 4-n-methylphenylacetylene 
• 20964-95-8 (2Z)-3-(benzylamino)-1,3-diphenyl-prop-2-en-1-one 

Downstream Products

• 108878-81-5 1,3-diethyl-4-phenyl-1,2,3-triazolium iodide 
• 111091-83-9 1-ethyl-3-benzyl-4-phenyl-[1,2,3]triazolium; iodide 
• 1111662-64-6 ethyl 4-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)benzoate 

Relevant academic research and scientific papers

Preparation of ruthenium azido complex containing a Tp ligand and ruthenium-catalyzed cycloaddition of organic azides with alkynes in organic and aqueous media: Experimental and computational studies

The catalytic activity of a series of ruthenium azido complexes containing Tp ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,5-disubstituted 1,2,3-triazoles. The complex Tp(PPh3)(EtNH2)RuN3 (2, Tp = HB(pz)3, pz = pyrazolyl) was found to be an effective catalyst for the cycloaddition reactions. In the presence of complex 2, azides reacted with a range of terminal alkynes containing various functionalities to selectively produce 1,5-disubstituted 1,2,3-triazoles. Theoretical calculations support the proposed mechanism.

Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air

We developed a highly regioselective base-induced synthesis of N2-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an SN2-like mechanistic pathway to explain the high N2-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72–90%).

Multi-component reaction for the preparation of 1,5-disubstituted 1,2,3-triazoles by in-situ generation of azides and nickel-catalyzed azide-alkyne cycloaddition

An efficient one-pot procedure combining bromide conversion into azide followed by NiAAC for the preparation of 1,5-disubstituted 1,2,3-triazoles has been developed. This procedure prevents the use of isolated azides, which are insufficiently commercially

Copper-Catalyzed Decarboxylative Cycloaddition of Propiolic Acids, Azides, and Arylboronic Acids: Construction of Fully Substituted 1,2,3-Triazoles

A copper-catalyzed decarboxylative cycloaddition of propiolic acids, azides, and arylboronic acids is described. The present reaction provides an efficient and convenient method for the synthesis of various fully substituted 1,2,3-Triazoles from readily available starting materials. A possible mechanism is proposed.

Ag-NHC anchored on silica: An efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis

A silica-supported silver complex, Ag-NHC@SiO2, was prepared by an anchoring coordination technique, which was successfully employed for the click reaction under mild reaction conditions. The protocol offered the remarkable advantages of operat

Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles by 1,3-dipolar cycloaddition: Role of Er(OTf)3, ionic liquid and water

A simple procedure to obtain 1,5-disubstituted 1,2,3-triazoles, using the Er(OTf)3/[mpy]OTf/H2O catalytic system is described. The reaction proceeds through an eliminative azide–olefin cycloaddition (EAOC) offering a highly regiosele

Novel synthesis of 1,5-disubstituted-1,2,3-triazolines catalysed by Zepto magnetic microspheres under the influence of a rotating magnetic field

The novel reactor has been designed to perform chemical reactions under the influence of a magnetic field generated by alternating magnetic poles as a function of time. The system was successfully employed to synthesize a series of 1,5-disubstituted-1,2,3-triazolines via the regioselective [3 + 2] cycloaddition reactions between alkyl/aryl azides and nitroolefins catalysed by Zepto (para magnetic ultra-blue carboxy functionalized) microspheres (bead diameter 2.5 μm). All of the reactions went smoothly without any adverse effect on nitro, cyano, thienyl, hydroxy, halogens, and ether functions at 25 ± 2 °C and afforded 82%-99% pure products at a magnetic field of 18.99 mT and an exposure time of 180-240 min. The influence of the magnetic force exerted on the magnetic materials was found to enhance the catalytic activity of microspheres. The catalyst could easily be separated by simple centrifugation, which could be reused for at least 15 runs with no loss in activity.

Multi-component reaction-functionalized chitosan complexed with copper nanoparticles: An efficient catalyst toward A3 coupling and click reactions in water

A novel bio-nanocomposite nanocatalyst with highly dispersed particles is synthesized through covalent functionalization of chitosan biopolymer by the multicomponent reaction (MCR) strategy. Surface functionalization of chitosan through MCR is led to the

Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation

The prevalence of 1,3-dipolar cycloadditions of azides and alkynes within both biology and chemistry highlights the utility of these reactions. However, the use of a copper catalyst can be prohibitive to some applications. Consequently, we have optimized

CuO-Nanoparticles Catalyzed Synthesis of 1,4-Disubstituted-1,2,3-Triazoles from Bromoalkenes

Abstract: A novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles. A library of 1,4-disubstituted 1,2,3-triazoles has been constructed with good to excellent yields. Graphical Abstract: SynopsisA novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles. A library of 1,4-disubstituted 1,2,3-triazoles has been constructed with good to excellent yields.[Figure not available: see fulltext.].