70380-30-2

Usage

Uses

Used in Organic Synthesis:
1-benzyl-4-(bromomethyl)-1H-1,2,3-triazole is used as a building block in organic synthesis for the creation of various organic compounds. The bromomethyl group allows for further chemical modifications, making it a valuable intermediate in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
1-benzyl-4-(bromomethyl)-1H-1,2,3-triazole is used as a starting material or intermediate in the development of pharmaceuticals. Its unique structure and potential biological activity make it a promising candidate for the design and synthesis of new drugs with therapeutic applications.
Used in Agricultural Applications:
1-benzyl-4-(bromomethyl)-1H-1,2,3-triazole may also find use in the agricultural industry, potentially serving as a component in the development of agrochemicals, such as pesticides or herbicides, due to its chemical properties and reactivity.

Upstream product

• 106-96-7 propargyl bromide 
• 622-79-7 benzyl azide 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 28798-81-4 (1-benzyl-[1,2,3]triazol-4-yl)methanol 

Downstream Products

• 27808-16-8 4-methyl-1H-(1,2,3)-triazole 
• 1442449-79-7 C₁₆H₂₅N₅ 
• 1472651-87-8 4-(azidomethyl)-1-benzyl-1H-1,2,3-triazole 
• 1472651-91-4 1-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-4-butyl-5-iodo-1H-1,2,3-triazole 
• 1639236-90-0 C₂₁H₂₁N₃O₃ 
• 1639236-83-1 C₂₀H₂₁N₃O₄ 
• 1639236-88-6 C₂₀H₂₁N₃O₃ 

Relevant academic research and scientific papers

Copper(ii) complexes ofN-propargyl cyclam ligands reveal a range of coordination modes and colours, and unexpected reactivity

The coordination chemistry ofN-functionalised cyclam ligands has a rich history, yet cyclam derivatives with pendant alkynes are largely unexplored. This is despite the significant potential and burgeoning application ofN-propargyl cyclams and related com

A Class of FeIII Macrocyclic Complexes with Alcohol Donor Groups as Effective T1 MRI Contrast Agents

Early studies suggested that FeIII complexes cannot compete with GdIII complexes as T1 MRI contrast agents. Now it is shown that one member of a class of high-spin macrocyclic FeIII complexes produces more intense contrast in mice kidneys and liver at 30 minutes post-injection than does a commercially used GdIII agent and also produces similar T1 relaxivity in serum phantoms at 4.7 T and 37 °C. Comparison of four different FeIII macrocyclic complexes elucidates the factors that contribute to relaxivity in vivo including solution speciation. Variable-temperature 17O NMR studies suggest that none of the complexes has a single, integral inner-sphere water that exchanges rapidly on the NMR timescale. MRI studies in mice show large in vivo differences of three of the FeIII complexes that correspond, in part, to their r1 relaxivity in phantoms. Changes in overall charge of the complex modulate contrast enhancement, especially of the kidneys.

Catalytic performance of Cu(II)-supported graphene quantum dots modified NiFe2O4 as a proficient nano-catalyst in the synthesis of 1,2,3-triazoles

Abstract: NiFe2O4 nanoparticles are modified by graphene quantum dots (GQDs) and utilized to stabilize the Cu(II) nanoparticles as a novel magnetically retrievable catalytic system (Cu(II)/GQDs/NiFe2O4) for gree

Design, synthesis, and functional evaluation of a novel series of phosphonate-functionalized 1,2,3-triazoles as positive allosteric modulators of α7 nicotinic acetylcholine receptors

The α7 nicotinic acetylcholine receptor is a pentameric ligand-gated ion channel widely distributed in the central nervous system, mainly in the hippocampus and cortex. The enhancement of its activity by positive allosteric modulators (PAMs) is a promising therapeutic strategy for cognitive deficits and neurodegenerative disorders. With the aim of developing novel scaffolds with PAM activity, we designed and synthesized a series of phosphonate-functionalized 1,4-disubstituted 1,2,3-triazoles using supported copper nanoparticles as the cycloaddition reaction catalyst and evaluated their activity on α7 receptors by single-channel and whole-cell recordings. We identified several triazole derivatives that displayed PAM activity, with the compound functionalized with the methyl phosphonate group being the most efficacious one. At the macroscopic level, α7 potentiation was evidenced as an increase of the maximal currents elicited by acetylcholine with minimal effects on desensitization, recapitulating the actions of type I PAMs. At the single-channel level, the active compounds did not affect channel amplitude but significantly increased the duration of channel openings and activation episodes. By using chimeric and mutant α7 receptors, we demonstrated that the new α7 PAMs share transmembrane structural determinants of potentiation with other chemically nonrelated PAMs. To gain further insight into the chemical basis of potentiation, we applied structure-activity relationship strategies involving modification of the chain length, inversion of substituent positions in the triazole ring, and changes in the aromatic nucleus. Our findings revealed that the phosphonate-functionalized 1,4-disubstituted 1,2,3-triazole is a novel pharmacophore for the development of therapeutic agents for neurological and neurodegenerative disorders associated with cholinergic dysfunction.

Synthesis, characterization, and investigation of catalytic activity of copper(II) porphyrin graphene oxide for azide–alkyne cycloaddition

Abstract: A covalently cross-linked graphene oxide (GO) catalyst was prepared by a cross-linking process using nucleophilic reaction of copper(II)‐coordinated 5,10,15,20-tetrakis(aminophenyl)porphyrin (CuPPh) with carboxyl groups at the edges of GO (GO–CuPPh). The structure of the catalyst was characterized using different techniques such as Fourier-transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive x-ray spectroscopy (EDS), thermogravimetric analysis (TGA), and inductively coupled plasma (ICP) spectroscopy. All analyses confirmed successful covalent immobilization of CuPPh on GO. The activity of the catalyst was then studied for synthesis of 1,4-disubstituted 1,2,3-triazoles derivatives by reaction of various aryl azides and different terminal alkynes in mild reaction condition with good to excellent yield. Graphical abstract: [Figure not available: see fulltext.].

Cu nanoparticles immobilized on modified magnetic zeolite for the synthesis of 1,2,3-triazoles under ultrasonic conditions

Magnetically recoverable copper nanoparticle-loaded natural zeolite (CuNPs/MZN) as an efficient catalyst was synthesized. The Fe3O4 magnetic nanoparticles were immobilized into the pores of natural clinoptilolite zeolite, which were

Copper(I)-Chelated Cross-Linked Cyclen Micelles as a Nanocatalyst for Azide-Alkyne Cycloaddition in Both Water and Cells

Featuring the dendrimer-like properties, the cross-linked small-molecule micelles (cSMs) have been shown to be a good alternative to dendrimers in many applications. Following this trend, herein the copper(I)-chelated cross-linked cyclen micelles (Cu

Chiral salen Mn (III) immobilized on ZnPS-PVPA through alkoxyl-triazole for superior performance catalyst in asymmetric epoxidation of unfunctionalized olefins

Chiral salen Mn (III) catalysts anchored onto ZnPS-PVPA via click chemistry are prepared and applied in asymmetric epoxidations of unfunctionalized olefins. Superior catalytic performances (conv%, up to >99; ee%, up to >99) are achieved in the epoxidations of α-methylstyrene, styrene, indene and 1-octene. According to 6-cyano-2,2-dimethylchromene and 6-nitro-2,2-dimethylchromene, configuration of epoxides are reversed. And then the catalysts are selective in not only oxidative systems, but also substrates. Moreover, superior reusability (yield, 82%; ee, 86%) after recycling for nine times could also be obtained, which provide the potential application in industry.

Asymmetric epoxidation of unfunctionalized olefins catalyzed by chiral salen-Mn (III) immobilized on alkoxyl-modified ZnPS-PVPA

Novel layered heterogeneous chiral salen Mn (III) catalysts anchored onto ZnPS-PVPA by means of click chemistry are synthesized and employed in asymmetric epoxidations of unfunctionalized olefins. The catalysts manifest superior catalytic performances (conv%, up to >99; ee%, up to >99) according to the epoxidations of α-methylstyrene, styrene, indene and 1-octene. But for 6-cyano- 2,2-dimethylchromene and 6-nitro-2,2-dimethylchromene, configuration of epoxides are reversed. Moreover, the catalysts could still indicate comparable properties (yield, 82%; ee, 86%) after recycling for nine times and excellent functions in large-scale reactions, which paves the way for the application in industry.

Synthesis, spectroscopic characterization, and DFT studies of 1,2,3-triazole-based organosilicon compounds

A series of triorgnosilicon compounds containing 1,2,3-triazole cores, tris(trimethylsilyl)ethyl) 1,2,3-triazoles (TTMSTs), tris(dimethyl(phenyl)silyl)ethyl) 1,2,3-triazoles (TDMPSTs), and bis(trimethylsilyl)vinyl) 1,2,3-triazoles (BTMSVTs) was synthesized and characterized by elemental analysis, FT-IR, 1H, 13C NMR spectroscopy, and density functional theory (DFT). The structure of the synthesized compounds was optimized using the B3LYP method of DFT at 6–311++G(d) basis set. Conjugate interactions or charge transfer in molecular systems was investigated using natural bond orbital (NBO) analysis. In addition, the FMOs (frontier molecular orbitals) and the associated band gaps were calculated and depicted. The mapped molecular electrostatic potential (MEP) surfaces of the title compounds were also calculated with the same level of theory.