62284-30-4

Usage

Uses

Used in Organic Synthesis:
2-fluorobenzyl azide is used as a reagent for introducing azide functional groups into organic molecules, which is crucial for the synthesis of various complex organic compounds and materials.
Used in Chemical Research:
In the field of chemical research, 2-fluorobenzyl azide serves as a valuable building block for creating fluorinated compounds, which are important in pharmaceuticals, agrochemicals, and materials science due to the unique properties conferred by fluorine substitution.
Used in Pharmaceutical Industry:
2-fluorobenzyl azide is used as a key intermediate in the synthesis of pharmaceuticals, where the introduction of azide and fluorine functionalities can enhance the biological activity and pharmacokinetic properties of drug candidates.
Used in Materials Science:
In materials science, 2-fluorobenzyl azide is utilized for the development of novel materials with tailored properties, such as improved stability, reactivity, or specific interactions, by incorporating azide and fluorinated moieties into their structures.
Safety Considerations:
Given the potential explosiveness of azide compounds, 2-fluorobenzyl azide must be handled with extreme caution. It is essential to follow proper safety measures and handling procedures to minimize the risk of accidents during its use in various applications.

Upstream product

• 1159505-61-9 C₈H₇F₄NO₂S 
• 100-46-9 benzylamine 
• 36457-58-6 N-benzyl-1,1,1-trifluoromethanesulfonamide 
• 345-35-7 2-fluorobenzyl chloride 
• 446-48-0 o-fluorobenzyl bromide 
• 5651-83-2 3-methoxy-4-(prop-2-ynyloxy)benzaldehyde 
• 4648-54-8 trimethylsilylazide 
• 478163-07-4 2-fluorobenzyl methanesulfonate 
• 89-99-6 2-fluorobenzylamine 
• 446-51-5 2-fluorobenzyl alcohol 
• 446-52-6 2-Fluorobenzaldehyde 
• 134430-70-9 p-[18F]fluorobenzyl bromide 
• 659-46-1 4-[18F]fluorofluorobenzyl alcohol 
• 134430-72-1 [18F]4'-fluorobenzyl iodide 

Downstream Products

• 1093975-80-4 1-(2-fluorobenzyl)-4-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1H-1,2,3-triazole 
• 1093236-61-3 1-(2-fluorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid 
• 1093237-06-9 C₁₁H₉ClFN₃O 
• 1093236-56-6 ethyl 1-(2-fluorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate 
• 1621582-04-4 ethyl 1-(2-fluorobenzyl)-4-methyl-1H-1,2,3-triazole-5-carboxylate 
• 89-99-6 2-fluorobenzylamine 

Relevant academic research and scientific papers

Design and synthesis of novel diosgenin-triazole hybrids targeting inflammation as potential neuroprotective agents

Alzheimer's disease is a progressive neurodegenerative disease, and its incidence is expected to increase as the global population ages. Recent studies provide increasing evidence that inflammation plays a key role in the pathogenesis and progression of AD. Diosgenin, an active ingredient in Dioscorea nipponica Makino, is a promising bioactive lead compound in the treatment of Alzheimer's disease, which exhibited anti-inflammatory activity. To search for more efficient anti-Alzheimer agents, a series of novel diosgenin-triazolyl hybrids were designed, synthesized, and their neuroprotective effects against oxygen-glucose deprivation-induced neurotoxicity and LPS-induced NO production were evaluated. Most of these new hybrids displayed better activities than DIO. In particular, the promising compound L6 not only demonstrated an excellent neuroprotective effect but also showed the best anti-inflammatory activity. The structure-activity relationship study illustrated that the introduction of benzyl or phenyl triazole did improve the activity, and the introduction of benzyl triazole was better than that of phenyl triazole. The results we obtained showed that the diosgenin skeleton could be a promising structural template for the development of new anti-Alzheimer drug candidates, and compound L6 has the potential to be an important lead compound for further research.

Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives

ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.

Synthesis and muscarinic acetylcholine receptor (mAChR) antagonist activity of substituted piperazine-triazoles

This study describes synthesis of a series of piperazine-triazole derivatives and their ex vivo evaluation for preliminary muscarinic acetylcholine receptor (mAChR) blocking activity on rat ileum model. A molecule based on benzonitrile piperazine triazole scaffold showed good tissue relaxation and blocking of neurotransmitter ACh in the ex vivo experiment. Graphic abstract: [Figure not available: see fulltext.]

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.

Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors

A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25?μM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14?μM) was the most potent compound. Kinetic study of this compound revealed that compound 6f inhibited urease in an uncompetitive mode. Based on molecular modeling study, compound 6f pointed toward the bi-nickel center and stabilized by H-bond and T-shape π–π hydrophobic interactions with the critical residues His492 and Asp633. Moreover, it anchored to the helix-turn-helix motif in the active site cavity through interaction with His593 and Arg609. Consequently, it proposed that compound 6f through stabilization of active site flap inhibited urease activity.

Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies

The current study was aimed to discover potent inhibitors of α-glucosidase enzyme. A 25 membered library of new 1,2,3-triazole derivatives of hydrochlorothiazide (1) (HCTZ, a diuretic drug also being used for the treatment of high blood pressure) was synt

Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions

Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.

New 1,2,3-triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation

A new series of 1,2,3-triazole–(thio)barbituric acid hybrids 8a–n was designed and synthesized on the basis of potent pharmacophores with urease inhibitory activity. Therefore, these compounds were evaluated against Helicobacter pylori urease. The obtained result demonstrated that all the synthesized compounds, 8a–n, were more potent than the standard urease inhibitor, hydroxyurea. Moreover, among them, compounds 8a, 8c–e, 8g,h, and 8k,l exhibited higher urease inhibitory activities than the other standard inhibitor used: thiourea. Docking studies were performed with the synthesized compounds. Furthermore, molecular dynamic simulation of the most potent compounds, 8e and 8l, showed that these compounds interacted with the conserved residues Cys592 and His593, which belong to the active site flap and are essential for enzymatic activity. These interactions have two consequences: (a) blocking the movement of a flap at the entrance of the active site channel and (b) stabilizing the closed active site flap conformation, which significantly reduces the catalytic activity of urease. Calculation of the physicochemical and topological properties of the synthesized compounds 8a–n predicted that all these compounds can be orally active. The ADME prediction of compounds 8a–n was also performed.

A Nanosized Propeller-like Polyoxometalate-linked Copper(I)-Resorcin[4]arene for Efficient Catalysis

The design and assembly of polyoxometalate-resorcin[4]arene-based metal-organic molecular materials are particularly attractive for their elegant structures and potential functions. By applying a newly designed resorcin[4]arene ligand (TPC4R-II), a copper(I)-coordinated polyoxometalate-based metal-organic molecular material, namely, [CuI6(Br)3(TPC4R-II)3(PMo12O40)]·8H2O (1), was rationally assembled. Three copper(I)-coordinated resorcin[4]arenes are held together by a central [PMo12O40]3- to yield a supramolecular propeller. 1 features efficient catalytic performances for oxidation desulfurization (ODS) and azide-alkyne cycloaddition (AAC) reactions. This work affords a feasible method for the nanosized polyoxometalate-based metal-resorcin[4]arene assemblies by well combinating two types of large composites as well as low coordination metal cations.

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.