108717-96-0

Basic information

• Product Name: 1-Benzyl-4-phenyl-1H-1,2,3-triazole
• Synonyms: 1-Benzyl-4-phenyl-1H-1,2,3-triazole;1-BENZYL-4-PHENYL-1,2,3-TRIAZOLE
• CAS NO: 108717-96-0
• Molecular Formula: C₁₅H₁₃N₃
• Molecular Weight: 235.28382
• Mol File: 108717-96-0.mol
• Article Data: 378

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-Benzyl-4-phenyl-1H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-4-phenyl-1H-1,2,3-triazole(108717-96-0)
• EPA Substance Registry System: 1-Benzyl-4-phenyl-1H-1,2,3-triazole(108717-96-0)

Safety Data

• Hazardous Substances Data: 108717-96-0(Hazardous Substances Data)

Usage

General Description

1-Benzyl-4-phenyl-1H-1,2,3-triazole, also known as PBT, is a chemical compound with a triazole ring structure. It is a commonly used building block in the synthesis of pharmaceuticals and agrochemicals due to its diverse biological activities. PBT has been studied for its potential as an anti-cancer, anti-inflammatory, and anti-fungal agent, as well as its ability to inhibit enzymes involved in various disease processes. It is also used as a fluorescent probe for detecting bioactive molecules and as a ligand in coordination chemistry. PBT has shown promise as a versatile compound with potential applications in the fields of medicine, biology, and materials science.

Upstream product

• 100-39-0 benzyl bromide 
• 536-74-3 phenylacetylene 
• 122-78-1 phenylacetaldehyde 
• 622-79-7 benzyl azide 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 13294-34-3 2-phenyl-1-(1-pyrrolidinyl)ethene 
• 860002-66-0 1-benzyl-4-phenyl-5-iodo-1,2,3-triazole 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1135539-10-4 1-(methylsulfonyl)-4-phenyl-1H-1,2,3-triazole 
• 1219601-57-6 1-(p-tolylsulfonyl)triazole 
• 13146-23-1 copper(I) phenylacetylenide 
• 1024-41-5 benzyl tosylate 
• 766-97-2 4-n-methylphenylacetylene 

Downstream Products

• 33471-66-8 1-benzyl-4,5-diphenyl-1H-1,2,3-triazole 
• 1043419-87-9 4-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)benzoic acid ethyl ester 
• 1111662-40-8 1-(4-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phenyl)ethanoate 
• 1037412-71-7 1-benzyl-4-phenyl-5-(2-tolyl)-1H-1,2,3-triazole 
• 1037412-72-8 1-benzyl-4-phenyl-5-(3-tolyl)-1H-1,2,3-triazole 
• 1438890-61-9 iridium(III) bis[(1′-phenyl)1,2,3-triazolato-N,C^2′]-4,4′-bi-1H-1,2,3-triazole 1,1′-bis(phenylmethyl) hexafluorophosphate 
• 1037412-73-9 1-benzyl-5-(4-fluorophenyl)-4-phenyl-1H-1,2,3-triazole 
• 1043420-02-5 1-benzyl-5-(4-methylphenyl)-4-phenyl-1H-1,2,3-triazole 
• 1379671-45-0 1-benzyl-4-phenyl-5-(2-fluorophenyl)-1H-1,2,3-triazole 
• 1379671-50-7 1-benzyl-4-phenyl-5-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,3-triazole 
• 1352802-51-7 (C₆H₅)3CH₂CH₂C₂HN₃⁽¹⁺⁾*Br^(1-)=(C₆H₅)3CH₂CH₂C₂HN₃Br 
• 1352807-71-6 1-benzyl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium bis[(trifluoromethyl)sulfonyl]amide 

Relevant articles and documents

Copper(I)-Catalyzed Interrupted Click Reaction with TMSCF3: Synthesis of 5-Trifluoromethyl 1,2,3-Triazoles

We herein describe a Cu(I)-catalyzed interrupted click reaction, using (trifluoromethyl)trimethylsilane (TMSCF3) as a nucleophilic CF3 source, to synthesize 5-trifluoromethyl 1,2,3-triazoles in one step from readily available terminal alkynes and azides. The reaction shows complete regioselectivity, broad substrate scope, and good functional group tolerability. The application of the reaction has been demonstrated in the synthesis of a trifluoromethylated analog of antiepileptic drug rufinamide.

Cu-Al mixed oxide catalysts for azide-alkyne 1,3-cycloaddition in ethanol-water

Cu(Al)O mixed oxides, which are obtained by the calcination of Cu-Al layered double hydroxide (LDH), promote the formation of 1,2,3-triazoles from an alkyne-azide cycloaddition reaction (Huisgen-type reaction) with excellent yields using an EtOH-H2O mixture as the solvent under microwave heating. The yield of the reaction is the result of both heterogeneous and homogeneous catalytic processes, as a consequence of capturing Cu(ii) from the material by sodium ascorbate. Although the appropriate reaction conditions were employed (EtOH-H2O, 80 °C, MW, 10 min), the reconstruction of LDH by the so-called memory effect was not observed.

Metal-Organic Framework Capillary Microreactor for Application in Click Chemistry

A Cu/PMA-MIL-101(Cr) metal-organic-framework-coated microreactor has been applied in the 1,3-dipolar cycloaddition of benzyl azide and phenylactetylene (click chemistry). The Cu/PMA-MIL-101(Cr) catalyst was incorporated by using a washcoating method. The

A Mechanochemically Triggered "click" Catalyst

"Click" chemistry represents one of the most powerful approaches for linking molecules in chemistry and materials science. Triggering this reaction by mechanical force would enable site- and stress-specific "click" reactions - a hitherto unreported observation. We introduce the design and realization of a homogeneous Cu catalyst able to activate through mechanical force when attached to suitable polymer chains, acting as a lever to transmit the force to the central catalytic system. Activation of the subsequent copper-catalyzed "click" reaction (CuAAC) is achieved either by ultrasonication or mechanical pressing of a polymeric material, using a fluorogenic dye to detect the activation of the catalyst. Based on an N-heterocyclic copper(I) carbene with attached polymeric chains of different flexibility, the force is transmitted to the central catalyst, thereby activating a CuAAC in solution and in the solid state.

Recoverable Cu/SiO2 composite-catalysed click synthesis of 1,2,3-triazoles in water media

An eco-friendly multicomponent reaction for the synthesis of 1,2,3-triazoles using a recoverable and recyclable Cu/SiO2 composite as the catalyst is reported. The reaction proceeds by mixing the benzyl halide, sodium azide, the alkyne and the catalyst in an aqueous medium to afford the desired products in excellent yields. The heterogeneous catalytic system showed high efficiency, performing the multicomponent Huisgen reaction in a green approach based on recoverability, recyclability and avoidance of waste. Microwave irradiation was also applied, substituting for conventional heating, resulting in excellent yields of the products with a dramatic reduction in the reaction time.

Synthesis of Chiral Nematic Mesoporous Metal and Metal Oxide Nanocomposites and their Use as Heterogeneous Catalysts

We report the synthesis of chiral nematic mesoporous metal and metal oxide nanocomposites containing zinc or copper prepared through a vacuum-assisted loading of the metal precursor into a chiral nematic mesoporous silica template followed by high-tempera

Azide–Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex

A highly efficient and environmentally benign protocol for copper-catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New copper(I) complexes bearing NHC ligands decorated with bulky hexafluoroisopropylalk

Regiospecific solid-phase synthesis of substituted 1,2,3-triazoles

A traceless and regiospecific solid-phase synthesis of substituted 1,2,3-triazoles is developed using polystyrene-sulfonyl hydrazide resin. The chemistry is applicable to combinatorial library synthesis.

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

Convergent synthesis of trifunctional molecules by three sequential azido-type-selective cycloadditions

A facile strategy for the synthesis of trifunctional molecules involving three sequential selective triazole-forming reactions is proposed. This method exploits three kinds of mechanistically different azido-type-selective cycloadditions. Three different azidophiles could be efficiently connected to a triazido platform molecule with three types of azido groups in a consecutive manner, which rendered a practical trifunctional molecule readily available.

Cu(i) coordination polymers (CPs) as tandem catalysts for three-component sequential click/alkynylation cycloaddition reaction with regiocontrol

To expand coordination polymers (CPs) as solid catalysts to selectively catalyze the three-component tandem click/alkynylation reaction for their fully substituted triazole skeletons, two Cu(i)-based CPs (CuI-CPs), [CuBr(aas-TPB)]n (

Fe3O4@ZIF-8: Magnetically recoverable catalysts by loading Fe3O4 nanoparticles inside a zinc imidazolate framework

A simple methodology for encapsulating ca. 10 nm-sized superparamagnetic Fe3O4 nanoparticles in zeolitic imidazolate frameworks (ZIF-8) crystals was developed. The corresponding Fe3O4@ZIF-8 heterostructured mate

Sol-gel entrapped Cu in a silica matrix: An efficient heterogeneous nanocatalyst for Huisgen and Ullmann intramolecular coupling reactions

A recyclable catalytic system has been developed that comprises an inorganic polymer matrix consisting of non-functionalized silica, which encapsulates copper by direct interaction with the matrix. Cu is fixed to a silica support of nanometric dimensions by physical entrapment within a silica sol-gel matrix. Samples with different Cu loadings were studied in order to maximize and optimize the amount of entrapped Cu within the silica matrix. This entrapment limits the diffusion of the metal to the solution, thus ensuring negligible contamination of the product by the metal while simultaneously providing a stabilizing environment. This robust and versatile heterogeneous catalyst was evaluated in Huisgen and Ullmann intramolecular coupling reactions.

Hydrosoluble Cu(i)-DAPTA complexes: Synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide-alkyne cycloaddition click reaction

New hydrosoluble and air-stable Cu(i) halide compounds, viz. [CuX(DAPTA)3] (1) and (2), and [Cu(μ-X)(DAPTA)2]2 (3) and (4) (X = Br or I, in this order), have been prepared by reacting Cu(i) halide (i.e., bromide or iodide)

Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system

A copper(I) catalyst in a mixture of the ionic liquid [bmim][BF 4] and water, can effect three-component reaction of halides, sodium azide and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good to high yields. The method is efficient and environmentally friendly.

DABCO/AcOH Jointly Accelerated Copper(I)-Catalysed Cycloaddition of Azides and Alkynes on Water at Room Temperature

An expeditious room temperature protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal alkynes and substituted azides has been achieved using the combination of CuSO4-ascorbate/1,4-diazabicyclo[2.2.2]octane/acetic acid. This expeditious protocol is applicable to aryl, alkyl, and sulfonyl azides. Acetic acid accelerates the protonation of cuprated triazole and thus avoids the possible side reactions. Devoid of acetic acid, the reaction pathway alters to the ketinimine route and results in the formation of sulfonamides.

Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe3O4 MNPs in a water/PEG300 system

A highly dispersible and magnetically recoverable Cu-PEI@Fe3O4 MNPs catalyst was prepared and success-fully applied in one-pot three-component coupling of terminal alkynes, sodium azide, and alkyl bromides/chlorides in water to give

Synthesis of 1,2,3-triazolyl-5-diethylphosphonate by domino reaction

The synthesis of 1,2,3-triazolyl-5-diethylphosphonate was studied by the domino reaction of benzyl azide, phenylacetylene and diethyl phosphite. The effect of the reaction stoichiometry, the atmosphere and the amount of the catalyst were investigated.

Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis of 5-Alkynyl-1,2,3-triazoles

A copper(I)-catalyzed tandem CuAAC/alkynylation reaction of various alkynes, organic azides, and bromoalkynes to provide rapid access to 5-alkynyl-1,2,3-triazoles has been developed. The reaction proceeded via a copper-catalyzed alkyne azide cycloaddition

Green methodologies for copper(I)-catalyzed azide-alkyne cycloadditions: A comparative study

Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1H-1,

Dicationic 1,3-Bis(1-methyl-1H-imidazol-3-ium) Propane Copper(I) Dibromate : Novel Heterogeneous Catalyst for 1,3-Dipolar Cycloaddition

Abstract: We disclose synthesis of a novel dicationic 1,3-bis(1-methyl-1H-imidazol-3-ium) propane copper(I) dibromate [Bis-(MIM)](CuBr2)] and explored its potential as a heterogeneous catalyst in 1,3-dipolar cycloaddition for regioselective synthesis of 1, 4-disubstituted-1,2,3- triazoles in excellent yields in ethanol: water (60:40%) system at 80°C. The noteworthy feature of the protocol includes in situ generation of aryl azides by azotisation of aryl as well as alkyl halides with sodium azide thereby enduring facile 1,3-dipolar cycloaddition with terminal alkynes. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis of Polysubstituted Imidazoles and Pyridines via Samarium(III) Triflate-Catalyzed [2+2+1] and [4+2] Annulations of Unactivated Aromatic Alkenes with Azides

Samarium(III) triflate-catalyzed [2+2+1] and [4+2] annulations have been identified for the preparation of fully substituted imidazoles and 2,3,5-trisubstituted pyridines from the readily available unactivated aromatic alkenes and azidomethyl aromatics. T

Copper-catalyzed decarboxylation/cycloaddition cascade of alkynyl carboxylic acids with azide

A copper-catalyzed decarboxylation/cycloaddition cascade of alkynyl carboxylic acids with azide has been developed. This reaction exhibits good functional group tolerance and wide substrate scope, provides an efficient way to construct 1,4-disubstituted 1

Synthesis and in vitro cytotoxicity and antibacterial activity of novel1,2,3-triazol-5-yl-phosphonates

Novel1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.

A-21·CuI as a catalyst for Huisgen's reaction: About iodination as a side-reaction

The polymer-supported catalyst Amberlyst A-21·CuI has found many applications in copper(I)-catalyzed Huisgen's (CuAAC) and other reactions. This catalyst was found to be efficient and reusable for the formation of 1,4-disubstituted 1,2,3-triazoles. It was

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

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%).

Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition

In this paper, we report a novel magnetically separable silica coated copper nano-magnetite NHC-benzimi@Cu complex as heterogeneous catalyst for the multicomponent click reaction via Huisgen 1,3-dipolar cycloaddition reaction of alkyl or aryl halide, sodi