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1-Azido-4-fluorobenzene solution, with the molecular formula C6H4FN3, is a colorless to pale yellow liquid that serves as a reagent in organic chemistry. It is utilized for a variety of chemical transformations, particularly in the synthesis of pharmaceutical compounds and materials. The presence of the azide functional group endows 1-Azido-4-fluorobenzene solution with high reactivity, necessitating careful handling due to its potential explosive nature.

3296-02-4

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3296-02-4 Usage

Uses

Used in Pharmaceutical Synthesis:
1-Azido-4-fluorobenzene solution is used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to undergo various chemical reactions, contributing to the development of new drugs and therapeutic agents.
Used in Material Science:
In the field of material science, 1-Azido-4-fluorobenzene solution is employed as a reagent for the synthesis of novel materials, leveraging its reactive nature to create substances with unique properties for various applications.
Safety Precautions:
When working with 1-Azido-4-fluorobenzene solution, it is crucial to adhere to safety protocols. It should be stored and handled in a well-ventilated area, away from heat or ignition sources. Protective equipment such as gloves and safety goggles is mandatory to prevent skin contact and eye exposure. Moreover, measures should be taken to avoid accidental ingestion or inhalation, and disposal should follow local regulations for hazardous waste to mitigate environmental and health risks.

Check Digit Verification of cas no

The CAS Registry Mumber 3296-02-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,9 and 6 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3296-02:
(6*3)+(5*2)+(4*9)+(3*6)+(2*0)+(1*2)=84
84 % 10 = 4
So 3296-02-4 is a valid CAS Registry Number.

3296-02-4 Well-known Company Product Price

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  • Aldrich

  • (779253)  1-Azido-4-fluorobenzene solution  ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC)

  • 3296-02-4

  • 779253-10ML

  • 1,709.37CNY

  • Detail
  • Aldrich

  • (779253)  1-Azido-4-fluorobenzene solution  ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC)

  • 3296-02-4

  • 779253-50ML

  • 6,769.62CNY

  • Detail

3296-02-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Azido-4-fluorobenzene

1.2 Other means of identification

Product number -
Other names 4-Fluorophenyl azide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3296-02-4 SDS

3296-02-4Relevant academic research and scientific papers

Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1H-tetrazole (LQFM-096)

Cardoso, Carina S.,Silva, Daiany P. B.,Silva, Dayane M.,Florentino, Iziara F.,Fajemiroye, James O.,Moreira, Lorrane K. S.,Vasconcelos, José P.,Sanz, Germán,Vaz, Boniek G.,Li?o, Luciano M.,Lima, Danilo da S.,dos Santos, Fernanda Cristina A.,Menegatti, Ricardo,Costa, Elson A.

, p. 877 - 892 (2020)

The aim of this study was to design, synthesize and evaluate the potential analgesic and anti-inflammatory effects of 5-[1-(4-fluorphenyl)-1H-1,2,3-triazol-4-yl]-1H-tetrazole—(LQFM-096: a new triazole compound) as well as to elucidate its possible mechani

Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents

Chiarelli, Laurent R.,Fan, Dongguang,Han, Quanquan,Lu, Yu,Qiao, Chunhua,Shi, Rui,Stelitano, Giovanni,Wang, Bin,Huszár, Stanislav,Miku?ová, Katarína,Savková, Karin

supporting information, p. 14526 - 14539 (2021/10/26)

The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.

Synthesis and rational design of new appended 1,2,3-triazole-uracil ensembles as promising anti-tumor agents via in silico vegfr-2 transferase inhibition

Bhaskar, Kuthati,Hu, Anren,Hung, Sung-Jen,Raju, Atcha Krishnam,Rao, Vankadari Srinivasa,Reddy, Nadipolla Naresh,Reddy, Puchakayala Muralidhar,Rohini, Rondla,Sanjeev, Ananthula,Swamy, Merugu Kumara

, (2021/05/29)

Angiogenesis inhibition is a key step towards the designing of new chemotherapeutic agents. In a view to preparing new molecular entities for cancer treatment, eighteen 1,2,3-triazole-uracil ensembles 5a–r were designed and synthesized via the click reaction. The ligands were well characterized using1 H-,13 C-NMR, elemental analysis and ESI-mass spectrometry. The in silico binding propinquities of the ligands were studied sequentially in the active region of VEGFR-2 using the Molegro virtual docker. All the compounds produced remarkable interactions and potentially inhibitory ligands against VEGFR-2 were obtained with high negative binding energies. Drug-likeness was assessed from the ADME properties. Cytotoxicity of the test compounds was measured against HeLa and HUH-7 tumor cells and NIH/3T3 normal cells by MTT assay. Compound 5h showed higher growth inhibition activity than the positive control, 5-fluorouracil (5-FU), against both HeLa and HUH-7 cells with IC50 values of 4.5 and 7.7 μM respectively. Interestingly, the compounds 5a–r did not show any cytotoxicity towards the normal cell lines. The results advance the position of substituted triazoles in the area of drug design with no ambiguity.

Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents

Tang, Kai-Wei,Hsu, Wen-Li,Chen, Cheng-Ru,Tsai, Ming-Hsien,Yen, Chia-Jung,Tseng, Chih-Hua

, p. 3589 - 3599 (2021/03/03)

Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is

Triazole [5, 4-d] pyrimidone tricyclic compounds as well as preparation method and application thereof

-

Paragraph 0064; 0067-0070; 0073, (2021/07/09)

The invention relates to triazole [5, 4-d] pyrimidone tricyclic compounds as well as a preparation method and application thereof.The triazole [5, 4-d] pyrimidone tricyclic compounds are prepared by following steps: taking different substituted anilines a

Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes

Jana, Sampad,Adhikari, Sweta,Cox, Michael R.,Roy, Sudeshna

supporting information, p. 1871 - 1874 (2020/02/20)

α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid (TFA). This work provides the first regioselective method to access 4-fluoro-1,5-disubstituted-1,2,3-triazoles.

Biofilm inhibition and DNA binding studies of isoxazole-triazole conjugates in the development of effective anti-bacterial agents

Habib, Farhat,Alam, Shadab,Hussain, Afzal,Aneja, Babita,Irfan, Mohammad,Alajmi, Mohamed F.,Hasan, Phool,Khan, Parvez,Rehman, Md Tabish,Noman, Omar Mohammed,Azam, Amir,Abid, Mohammad

, (2019/10/14)

Isoxazole-triazole conjugates (8a-q) were synthesized using click chemistry approach and their biological activities were explored to develop novel antibacterial agents. In vitro antibacterial screening against Gram-positive as well as Gram-negative bacterial strains identified compounds 8b and 8m with potent inhibitory potential against selective bacterial cells. 8b showed IC50 value of 67.6 μg/mL against P. aeruginosa while 8m exhibited better activity against Gram-positive bacteria S. pneumoniae and E. faecalis having IC50 values 74.13 and 44.7 μg/mL, respectively. Effect on growth kinetics of the bacterial cells as well as cytotoxicity studies on human embryonic kidney cells (HEK293) further supports their biological potential. Compound 8m significantly inhibited biofilm formation of E. coli cells visualized by scanning electron microscopy (SEM) analysis. The interaction of these compounds with ctDNA, as their possible mode of action, was studied using multi-spectroscopic techniques and molecular docking. The data suggested that compound 8m intercalate in the minor groove of DNA.

New potent STS inhibitors based on fluorinated 4-(1-phenyl-1H-[1,2,3]triazol-4-yl)-phenyl sulfamates

Da?ko, Mateusz,Demkowicz, Sebastian,Rachon, Janusz,Biernacki, Karol,Aszyk, Justyna,Kozak, Witold,Mas?yk, Maciej,Kubiński, Konrad

, p. 1037 - 1044 (2019/12/03)

A series of fluorinated analogs based on the frameworks of 4-(1-phenyl-1H-[1,2,3]triazol-4-yl)-phenyl sulfamates have been synthesized as steroid sulfatase (STS) inhibitors. The design of chemical structures of new potential STS inhibitors was supported by molecular docking techniques to identify potential interactions between inhibitors and amino acid residues located in the STS active site. The STS inhibitory potency was evaluated on STS isolated from human placenta. We found that compounds substituted with fluorine atom at the meta position demonstrated the highest inhibitory effects in enzymatic STS assay. The most active analog 12e–inhibited STS enzyme with the IC50 value of 36 nM.

Design, synthesis and biological evaluation of homoerythrina alkaloid derivatives bearing a triazole moiety as PARP-1 inhibitors and as potential antitumor drugs

Li, Shuai,Li, Xin-yang,Zhang, Ting-jian,Kamara, Mohamed Olounfeh,Liang, Jing-wei,Zhu, Ju,Meng, Fan-hao

, (2019/11/11)

A series of homoerythrina alkaloid derivatives containing a 1,2,3-triazole moiety as PARP-1 inhibitors were designed and synthesized. And their anti-proliferative activity was further evaluated. Compound 10n had excellent activity to inhibit proliferation of A549 cells (IC50 = 1.89 μM), which was higher than harringtonine (IC50 = 10.55 μM), pemetrexed (IC50 = 3.39 μM), and rucaparib (IC50 = 4.91 μM). Furthermore, the selectivity index of compound 10n was higher than rucaparib and pemetrexed for lung cancer cells. Flow cytometry analysis showed that compound 10n significantly arrested the cell cycle in the S phase, then induced apoptosis of A549 cells (apoptosis rate is 46%), which effectively inhibited cell proliferation. Simultaneously, western blot analysis revealed that compound 10n could prevent the biosynthesis of PAR. Further analysis results revealed that compound 10n could inhibit the expression of cyclin A, down-regulate the expression of bcl-2/bax, activate caspase-3, and ultimately induce apoptosis of A549 cells. All the results indicated that compound 10n had potential research value as a novel PARP-1 inhibitor in antitumor, and it provided a new reference for further development of PARP-1 inhibitors.

Innovative three-step microwave-promoted synthesis of N-propargyltetrahydroquinoline and 1,2,3-triazole derivatives as a potential factor Xa (FXA) inhibitors: Drug design, synthesis, and biological evaluation.

Santana-Romo, Fabián,Lagos, Carlos F.,Duarte, Yorley,Castillo, Francisco,Moglie, Yanina,Maestro, Miguel A.,Charbe, Nitin,Zacconi, Flavia C.

, (2020/02/11)

The coagulation cascade is the process of the conversion of soluble fibrinogen to insoluble fibrin that terminates in production of a clot. Factor Xa (FXa) is a serine protease involved in the blood coagulation cascade. Moreover, FXa plays a vital role in the enzymatic sequence which ends with the thrombus production. Thrombosis is a common causal pathology for three widespread cardiovascular syndromes: acute coronary syndrome (ACS), venous thromboembolism (VTE), and strokes. In this research a series of N-propargyltetrahydroquinoline and 1,2,3-triazole derivatives as a potential factor Xa (FXa) inhibitor were designed, synthesized, and evaluated for their FXa inhibitor activity, cytotoxicity activity and coagulation parameters. Rational design for the desired novel molecules was performed through protein-ligand complexes selection and ligand clustering. The microwave-assisted synthetic strategy of selected compounds was carried out by using Ullmann-Goldberg, N-propargylation, Mannich addition, Friedel-Crafts, and 1,3-dipolar cycloaddition type reactions under microwave irradiation. The microwave methodology proved to be an efficient way to obtain all novel compounds in high yields (73–93%). Furthermore, a thermochemical analysis, optimization and reactivity indexes such as electronic chemical potential (μ), chemical hardness (η), and electrophilicity (ω) were performed to understand the relationship between the structure and the energetic behavior of all the series. Then, in vitro analysis showed that compounds 27, 29–31, and 34 exhibited inhibitory activity against FXa and the corresponding half maximal inhibitory concentration (IC50) values were calculated. Next, a cell viability assay in HEK293 and HepG2 cell lines, and coagulation parameters (anti FXa, Prothrombin time (PT), activated Partial Thromboplastin Time (aPTT)) of the most active novel molecules were performed to determine the corresponding cytotoxicity and possible action on clotting pathways. The obtained results suggest that compounds 27 and 29 inhibited FXa targeting through coagulation factors in the intrinsic and extrinsic pathways. However, compound 34 may target coagulation FXa mainly by the extrinsic and common pathway. Interestingly, the most active compounds in relation to the inhibition activity against FXa and coagulation parameters did not show toxicity at the performed coagulation assay concentrations. Finally, docking studies confirmed the preferential binding mode of N-propargyltetrahydroquinoline and 1,2,3-triazole derivatives inside the active site of FXa.

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