104926-74-1

Basic information

• Product Name: 1H-1,2,3-Triazole, 1-[(4-nitrophenyl)methyl]-4-phenyl-
• CAS NO: 104926-74-1
• Molecular Formula: C15H12N4O2
• Molecular Weight: 280.286
• Mol File: 104926-74-1.mol
• Article Data: 214

Chemical Properties

• CAS DataBase Reference: 1H-1,2,3-Triazole, 1-[(4-nitrophenyl)methyl]-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3-Triazole, 1-[(4-nitrophenyl)methyl]-4-phenyl-(104926-74-1)
• EPA Substance Registry System: 1H-1,2,3-Triazole, 1-[(4-nitrophenyl)methyl]-4-phenyl-(104926-74-1)

Safety Data

• Hazardous Substances Data: 104926-74-1(Hazardous Substances Data)

Upstream product

• 1680-44-0 4-phenyl-1H-1,2,3-triazole 
• 100-14-1 4-nitrobenzyl chloride 
• 536-74-3 phenylacetylene 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 17271-88-4 p-nitrobenzyl azide 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 4450-68-4 4-nitrobenzyl tosylate 
• 619-73-8 4-nitrobenzyl chloride 
• 7409-30-5 p-nitrobenzylamine 
• 588-73-8 (Z)-β-bromostyrene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 637-44-5 phenylpropyolic acid 
• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 

Downstream Products

• 104951-48-6 4-((4-phenyl-1H-1,2,3-triazole-1-yl)methyl)aniline 
• 104951-50-0 1-(p-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole 

Relevant articles and documents

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Readily prepared copper(II) immobilized on layered double hydroxide has been found to effectively catalyse the 1,3-dipolar cycloaddition (CuAAC) of a variety terminal alkynes and benzyl azides generated in situ from sodium azide and benzyl halides furnishing the corresponding 1,2,3-triazoles in excellent yields. The advantages of the protocol are short reaction time, mild reaction conditions, reusability of the catalyst and applicability to a wide range of substrates.

Redox Instability of Copper(II) Complexes of a Triazine-Based PNP Pincer

The new Cu(I) complex [Cu(PNPNTPh-Ph)Cl] (1) containing the tridentate PNP pincer ligand N,N′-bis(diphenylphosphino)-2,6-diamino-4-phenyl-1,3,5-triazine was obtained from the reaction of [Cu(SMe2)Cl]n with the ligand as ether solvate 1.0.5Et2O. 1 was independently obtained from a reaction mixture containing the ligand and the Cu(II) precursor CuCl2.2H2O in 50 % yield alongside with the Cu(II) coordination polymer [Cu(O2PPh2)2]n (2). From the reaction of Cu(NO3)2 ? 3H2O with PNPNTPh-Ph in the presence of pyridine the complexes [Cu(O2PPh2)2(Py)2(H2O)] (3), [Cu(O2PPh2)(Py)2(NO3)]2 (4), and [Cu(Py)4(NO3)2].Py (5), were obtained, 2, 3, and 4 contain diphenyl-phosphinate ligands. The underlying redox reaction of the ligand and Cu(II) yielding the oxidised ligands observed in the by-products and the Cu(I) product complex was further studied using electrochemistry and UV-vis spectroelectrochemistry. Attempts to synthesise the Cu(II) complex [Cu(PNPNTPh-Ph)(NO3)2] (6) in a mechanochemical experiment gave evidence for this unprecedented species from ESI-MS(+) and EPR spectroscopy but also revealed its very high sensitivity to air and moisture. The catalytic activity of 1 was investigated in the azide-alkyne cycloaddition yielding various 1-benzyl-4-phenyl-1H-1,2,3-triazoles. The environmentally benign (“green”) and cheap EtOH/H2O solvent mixture turned out to be very suitable. Melting points, FT-IR, and NMR spectra of the triazole products were analysed.

Copper(I) Complexes Bearing Carbenes beyond Classical N-Heterocyclic Carbenes: Synthesis and Catalytic Activity in "click Chemistry"

The synthesis and characterization of abnormal N-heterocyclic carbene, cyclic (alkyl)(amino)carbene, and mesoionic carbene copper(I) complexes are reported. These organometallic species are obtained via a versatile and inexpensive synthetic pathway using

Immobilized copper nanoparticles on nitrogen-rich porous activated carbon from egg white biomass: A robust hydrophilic-hydrophobic balance catalyst for click reaction

Biomass conversion to carbonaceous materials and their use in various applications, such as capacitors, catalyst supports, and adsorbents, have attracted considerable attention from the viewpoint of green chemistry. In this regard, chicken egg white is on

Dinuclear Cu(I) Halides with Terphenyl Phosphines: Synthesis, Photophysical Studies, and Catalytic Applications in CuAAC Reactions

Several dinuclear terphenyl phosphine copper(I) halide complexes of composition [CuX(PR2Ar′)]2 (X = Cl, Br, I; R = hydrocarbyl, Ar′ = 2,6-diarylterphenyl radical), 1-5, have been isolated from the reaction of CuX with 1 equiv of the phosphine ligand. Most

Synthesis of Fe3O4-DOPA-Cu Magnetically Separable Nanocatalyst: A Versatile and Robust Catalyst for an Array of Sustainable Multicomponent Reactions under Microwave Irradiation

Abstract: Herein, we are reporting a facile route to synthesize magnetically separable copper loaded L-DOPA functionalized magnetite nanoparticles (Fe3O4-DOPA-CuNPs), which are well characterized by FT-IR, PXRD, SEM, EDAX, HRTEM, XPS, TGA and VSM techniques. This single catalyst exhibits excellent catalytic activity towards (i) synthesis of DHPMs via Biginelli reaction (ii) synthesis of imidazoles (iii) synthesis of 2-amino-4H-chromenes (iv) 1,2,3-triazole derivatives by ‘Click reaction’ under microwave irradiation (MWI). Interestingly it can be easily recovered and reused for subsequent cycles for above mentioned four important multicomponent reactions without any significant decrease in its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.].

(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and Mono- Or disubstituted alkynes

A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC

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.

Synthesis of copper nanoparticles supported on MoO3 using Sun spurge leaf extract and their catalytic activity

Copper nanoparticles supported on MoO3 (Cu NPs/MoO3) were prepared by a green method using Sun spurge leaf extract. Cu NPs/MoO3 nanoparticles were characterized by X-ray diffraction analysis, energy dispersive X-ray analysis, scanning electron microscope and transmission electron microscope. The catalytic activity of this well-defined material in three-component CuAAC reactions was tested to produce 1,4-disubstituted-1,2,3-triazoles in good to excellent yields in water as a green solvent. More importantly, the catalyst can be recovered and reused efficiently up to five consecutive cycles with no significant loss of catalytic activity.

Silver and copper nanoparticles stabilized on ionic liquids-functionalized polyhedral oligomeric silsesquioxane (POSS): Highly active and recyclable hybrid catalysts

Two novel heterogeneous hybrid catalysts were successfully synthesized using octa-aminopropyl polyhedral oligomeric silsesquioxane hydrochloride salt (OA-POSS) and ionic liquids, followed by immobilization of Cu and Ag nanoparticles. The obtained hybrid catalysts, Cu@POSS-ILs and Ag@POSS-ILs, were characterized using FT-IR, SEM, EDX, TEM, XRD and TGA. Catalytic studies demonstrated that Cu@POSS-ILs was an excellent catalyst for click reaction in aqueous medium. Furthermore, Ag@POSS-ILs was also exhibited to be an active catalyst for 4-nitrophenol (4-NP) reduction. Simple preparation and easy catalysts recovery and recyclability of Cu@POSS-ILs and Ag@POSS-ILs for at least 3 and 6 runs, respectively, without loss of catalytic activity could be considered as important advantageous from catalytic application point of view.

Continuous-flow azide-alkyne cycloadditions with an effective bimetallic catalyst and a simple scavenger system

A flow chemistry-based technique is presented herein for Cu(i)-catalyzed azide-alkyne cycloadditions with a copper on iron bimetallic system as the catalyst and iron powder as a readily available copper scavenger. The method proved to be rapid and safe as

Copper (I) complex of 2,9-dimethyl-1,10-phenanthroline: Synthesis, structure, and catalytic properties

A copper (I) complex containing 2,9-dimethyl-1,10-phenanthroline (dmph), [Cu(dmph)2]Cl·6H2O, was prepared by reaction of CuCl2·2H2O and 2,9-dimethyl-1,10-phenanthroline in an aqueous solution at pH = 11 and characterized using elemental analysis, IR, EDX and X-ray crystallography. The complex consists of a mononuclear copper (I) surrounded by four coordinating nitrogen atoms of two dmph ligands, one Cl? anion and six H2O molecules. This novel cupper (I) complex was used as a catalyst for alkyne-azide cycloaddition (CuAAC) reaction to produce several 1,2,3-triazoles in high yields. The presented catalytic system fulfils the requirements of “click chemistry” with its soft and appropriate conditions, notably in water as solvent with low catalyst amount without any co-catalyst or activator.

Cube-octameric silsesquioxane-mediated cargo copper Schiff base for efficient click reaction in aqueous media

The azide-alkyne cycloaddition reaction was investigated under catalytic conditions involving a copper(II) - polyhedral oligomeric silsesquioxane (POSS) - bridged Schiff base. This material demonstrated a high catalytic activity in organic synthesis of 1,4-triazoles. No additive such as a base or a reductant was required. Finally, recoverability and reusability of the POSS-bridged Schiff base-Cu(II) catalyst was analyzed.

Copper-loaded hypercrosslinked polymer decorated with pendant amine groups: A green and retrievable catalytic system for quick [3 + 2] Huisgen cycloaddition in water

A novel heterogeneous copper catalyst based on a 3D-network polymer containing pendant amine groups was synthesized via post-functionalization of the polymeric backbone followed by incorporation of copper(i) ions. Catalytic activity of the newly designed

Preparation and characterization of functionalized graphene oxide Cu (I) complex: A facile and reusable nanocatalyst for microwave assisted heterocyclization of alkyl halides with alkynes and sodium azide

In this research, preparation of functionalized graphene oxide copper (I) complex first involves a reaction of carboxylic groups on graphene oxide with the amino groups on 1,7-heptandiamine and isotoic anhydride, and subsequently treatment with copper iodide. The formed complex was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction spectroscopy (XRD), energy dispersive X- ray (EDX) and field emission scanning electron microscopy (FE-SEM) techniques. 1,2,3-triazoles were synthesized from reaction of alkyl halides, alkynes and sodium azide catalyzed by functionalized graphene oxide copper (I) complex under microwave irradiation in excellent yields. This procedure eliminates the need to handle organic azides.

One-pot three-component synthesis of 1,4-disubstituted 1H-1,2,3-triazoles using green and recyclable cross-linked poly(4-vinylpyridine)-supported copper sulfate/sodium ascorbate in water/t-BuOH system

Cross-linked poly(4-vinylpyridine)-supported copper sulfate, [P4-VP]CuSO4 as a green and recyclable, heterogeneous catalyst in the presence of sodium ascorbate (NaAsc), is reported for the regioselective synthesis of 1,4-disubstituted-1,2,3-tri

Arylhydrazone ligands as Cu-protectors and -catalysis promoters in the azide-alkyne cycloaddition reaction

A series of water soluble copper(ii) complexes, [Cu(κO1O2N-H2L1)(H2O)2]·2H2O (2), [Cu(κO-H3L1)2(H2O)4] (3), [Cu(κO-H4

Polyvinyl alcohol-stabilized cuprous oxide particles: efficient and recyclable heterogeneous catalyst for azide-alkyne cycloaddition in water at room temperature

Abstract The PVA-stabilized Cu2O particles were prepared using a novel and simple rout in aqueous medium at room temperature under aerobic conditions. Initially, Cu(II) ions were fixed in PVA matrix via complex formation with OH groups, subsequ

Crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes: A bio-nanoreactor with extremely high activity toward click-multi-component reactions

In the present study, we have designed a procedure for the synthesis of a bio-nanoreactor catalyst, crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes (CS NPs/MWCNT@Fe3O4), via an in situ ionotropic gelation method. The synthesized robust nanoreactor was fully characterized. Moreover, the catalytic activity was investigated towards the click-based multi-component reactions for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, trisubstituted imidazoles, and 1,2,3-triazoles in a green medium. Since the nanocatalyst can be recovered by applying an external magnetic field, which results in easy separation without filtration, and recycled several times without the loss of its significant activities, it shows admirable potential in reusable catalysis.

Natural phosphate-supported Cu(ii), an efficient and recyclable catalyst for the synthesis of xanthene and 1,4-disubstituted-1,2,3-triazole derivatives

Cu(NO3)2 supported on natural phosphate, Cu(ii)/NP, was prepared by co-precipitation and applied as a heterogeneous catalyst for synthesizing xanthenes (2-3 h, 85-97%) through Knoevenagel-Michael cascade reaction of aromatic aldehydes with 1,3-cyclic diketones in ethanol under refluxing conditions. It was further used for regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles (1-25 min, 95-99%) via a three-component reaction between organic halides, aromatic alkynes and sodium azide in methanol at room temperature. The proposed catalyst, Cu(ii)/NP, was characterized using X-ray fluorescence, X-ray diffraction, Fourier-transform infrared spectroscopy, scanning electron microscopy, Brunauer-Emmett-Teller, Barrett-Joyner-Halenda and inductively coupled plasma analyses. Compared to other reports in literature, the reactions took place through a simple co-precipitation, having short reaction time (85%), and high recyclability of catalyst (>5 times) without significant decrease in the inherent property and selectivity of catalyst. The proposed protocols provided significant economic and environmental advantages.

Dinuclear Copper(I) complexes of phenanthrolinyl-functionalized NHC ligands

We have prepared a number of phenanthroline-functionalized imidazolium and triazolium salts from 2-iodo-1,10-phenanthroline and imidazole and triazole derivatives. Simple reactions of these imidazolium salts with copper powder at room temperature have aff

Solvent-free copper-catalyzed azide-alkyne cycloaddition under mechanochemical activation

The ball-mill-based mechanochemical activation of metallic copper powder facilitates solvent-free alkyne-azide click reactions (CuAAC). All parameters that affect reaction rate (i.e., milling time, revolutions/min, size and milling ball number) have been

Anchoring Cu nanoparticles on functionalized multi-walled carbon nanotube for regioselective synthesis of 1,2,3-triazoles via click reaction

Unique properties of 1,2,3-triazoles on the one hand and necessity of usage of an efficient catalyst with fidelity in principles of green chemistry on the other hand impelled us to design and synthesis of a novel heterogeneous nanocatalyst (Cu@Arg-MWCNTs)

Ferromagnetic nanoparticle-supported copper complex: A highly efficient and reusable catalyst for three-component syntheses of 1,4-disubstituted 1,2,3-triazoles and C–S coupling of aryl halides

A new nanocatalyst was synthesized by immobilization of 4′-(4-hydroxyphenyl)-2,2′:6′,2″-terpyridine/CuI complex on ferromagnetic nanoparticles through a surface modification (FMNPs@SiO2-TPy-Cu). This heterogeneous catalyst was characterized using various techniques including Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The resulting nanocatalyst presented excellent catalytic activity for the regioselective syntheses of 1,4-disubstituted 1,2,3-triazoles and thioethers. The thermally and chemically stable, benign and economical catalyst was easily recovered using an external magnet and reused in at least five successive runs without an appreciable loss of activity.

Synthesis of copper containing polyaniline composites through interfacial polymerisation: An effective catalyst for Click reaction at room temperature

Polyaniline (PANI) supported Cu (Cu/PANI) catalyst served as an efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles via click chemistry approach. Herein, we have illustrated the development of two copp

CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level

The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM

Melamine-supported nickel oxide nanoparticles as a good alternative to conventional copper catalysts for the regioselective synthesis of triazole derivatives in water

Nickel oxide nanoparticles supported on melamine as a good alternative to conventional copper catalysts have been prepared and used for the regioselective synthesis of triazole derivatives in water. This catalyst can be reused several times without any si

Preparation, characterization and catalytic study of a nano-inorganic composite of CuO/NiO for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles in water

In this research, a nano-inorganic composite of CuO/NiO is prepared by co-precipitation method as an efficient recyclable nanocatalyst for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles in water. The catalyst was characterized by severa