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

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

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-Benzyl-4-phenyl-1H-1,2,3-triazole is used as a building block for the synthesis of various pharmaceuticals and agrochemicals due to its diverse biological activities and potential therapeutic effects.
Used in Cancer Research and Treatment:
PBT is used as an anti-cancer agent for its potential to target and inhibit the growth of cancer cells, making it a candidate for further research and development in oncology.
Used in Inflammation and Fungal Infection Management:
1-Benzyl-4-phenyl-1H-1,2,3-triazole is used as an anti-inflammatory and anti-fungal agent, leveraging its biological properties to manage inflammation and combat fungal infections.
Used in Enzyme Inhibition Studies:
PBT is utilized in research to inhibit specific enzymes involved in disease processes, offering a potential avenue for the development of targeted therapies.
Used in Fluorescent Probe Development:
As a fluorescent probe, 1-Benzyl-4-phenyl-1H-1,2,3-triazole is used for detecting and analyzing bioactive molecules, contributing to advancements in diagnostic techniques and biochemistry.
Used in Coordination Chemistry:
PBT serves as a ligand in coordination chemistry, facilitating the study and creation of new coordination compounds with potential applications in various scientific and industrial fields.

Upstream product

• 536-74-3 phenylacetylene 
• 622-79-7 benzyl azide 
• 637-44-5 phenylpropyolic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 100-46-9 benzylamine 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 932-88-7 1-iodo-2-phenylethyne 
• 17061-86-8 1-methoxy-4-(2-propynyloxy)benzene 
• 13146-23-1 copper(I) phenylacetylenide 
• 766-97-2 4-n-methylphenylacetylene 
• 1024-41-5 benzyl tosylate 
• 100-51-6 benzyl alcohol 
• 860002-66-0 1-benzyl-4-phenyl-5-iodo-1,2,3-triazole 

Downstream Products

• 936475-48-8 [Pd(C₆H₃(CH₂NMe₂)2)(1-benzyl-4-phenyl-1,2,3-triazole)](BF₄) 
• 936475-50-2 [Pt(C₆H₃(CH₂NMe₂)2)(1-benzyl-4-phenyl-1,2,3-triazole)](BF₄) 
• 1111662-42-0 2-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)pyridine 
• 1111662-41-9 4-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)benzonitrile 
• 1043420-02-5 1-benzyl-5-(4-methylphenyl)-4-phenyl-1H-1,2,3-triazole 
• 1111662-37-3 1-benzyl-5-(2-methoxyphenyl)-4-phenyl-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 
• 1127217-82-6 1-benzyl-5-(3,4-dimethoxyphenyl)-4-phenyl-1,2,3-triazole 
• 1262989-53-6 1-benzyl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium tetrafluoroborate 
• 1322619-41-9 [Re(2,2'-bipyridine)(carbonyl)3(1-benzyl-4-phenyl-1,2,3-triazole)][P(fluoride)6] 
• 1350539-19-3 1,5-diphenyl-4-benzyl-1H-1,2,3-triazole 
• 1352807-71-6 1-benzyl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium bis[(trifluoromethyl)sulfonyl]amide 
• 1352802-51-7 (C₆H₅)3CH₂CH₂C₂HN₃⁽¹⁺⁾*Br^(1-)=(C₆H₅)3CH₂CH₂C₂HN₃Br 

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.

Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition

Tris(2-benzimidazolylmethyl)amines have been found to be superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. Candidates bearing different benzimidazole N-substituents as well as benzothiazole and pyridyl ligand a

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.

Mechanistic insights into copper(I)-catalyzed azide-alkyne cycloadditions using continuous flow conditions

The copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click chemistry") was studied employing copper-in-charcoal (Cu/C) and a variety of copper metal sources as "heterogeneous" catalysts. The type and pretreatment conditions of the different copper sources on the CuAAC were investigated. In addition, the effect of copper leaching from the catalyst over time and in dependence on the reaction mixture composition was studied by ICP-MS analysis in the continuous flow mode. These investigations confirm a "homogeneous" mechanism and suggest surface layer copper(I) oxide as the catalytically active species in CuAAC chemistry involving zerovalent copper metal.

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

Novel ion-binding C3 symmetric tripodal triazoles: Synthesis and characterization

Novel C3 symmetric tripodal molecules were synthesized from cyclohexane 1,3,5-tricarboxylic acid. Utilizing click and Sonogashira reactions, ion-binding triazole and pyridazin-3(2H)-one units were incorporated to form polydentate ligands for ion complexation. The structures of the novel C 3 symmetric derivatives were extensively characterized by 1H, 13C and 2D NMR techniques along with HRMS and IR. The copper(I)-binding potentials of these ligands were investigated by using them as additives in model copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The copper(I) complexation ability of our compound was also proved by different spectroscopic methods, such as mass spectrometry, UV and NMR spectroscopy. Based on the mass spectrometric data all of the C3 symmetric ligands formed 1:1 complex with copper(I) ion. The specific role of C3 symmetric polydentate form in the complexation process was also discussed [Figure not available: see fulltext.]

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.

Synthesis of 1,4-disubstituted 1,2,3-triazoles via a three-component reaction in water in the presence of CuX (X = Cl, I)

(Chemical Equation Presented) Three-component reaction of alkyl halides, sodium azide and alkynes in water in the presence of CuX (X = Cl, I) afforded 1,4-disubstituted 1,2,3-triazoles in high yields. These reactions do not require any special precautions or existence of a reducing agent. The bistriazoles formed during the reaction can efficiently enhance the catalytic activity of the Cu(I) salts.

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.

Introducing the 4-Phenyl-1,2,3-Triazole Moiety as a Versatile Scaffold for the Development of Cytotoxic Ruthenium(II) and Osmium(II) Arene Cyclometalates

Herein we report the synthesis, anticancer potency in vitro, biomolecule interaction, and preliminary mode of action studies of a series of cyclometalated 1,2,3-triazole-derived ruthenium(II) (2a-e) and osmium(II) (3a-e) organometallics of the general for