766-80-3

Usage

Uses

Used in Organic Synthesis:
3-Chlorobenzyl bromide is used as a starting reagent for the synthesis of various organic compounds. Its reactivity and functional groups make it a valuable intermediate in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Synthesis of Benzyl Thioethers:
3-Chlorobenzyl bromide is used as a key intermediate in the synthesis of symmetrical and unsymmetrical benzyl thioethers. These thioethers have potential applications in the development of new drugs, agrochemicals, and materials.
Used in the Synthesis of 1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole Dihydrochloride:
3-Chlorobenzyl bromide is used as a starting reagent in the synthesis of 1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole dihydrochloride, a compound with potential biological activities. This synthesis demonstrates the versatility of 3-chlorobenzyl bromide in the preparation of complex organic molecules.

InChI:InChI=1/C7H6BrCl/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

Upstream product

• 506-68-3 bromocyane 
• 876476-09-4 (3-bromo-benzyl)-(3-chloro-benzyl)-methyl-amine 
• 854392-02-2 (3-chloro-benzyl)-methyl-(4-nitro-benzyl)-amine 
• 108-41-8 1-chloro-3-methylbenzene 
• 873-63-2 m-chlorobenzyl alcohol 
• 70450-41-8 1-chloro-3-(iodomethyl)benzene 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 7726-95-6 bromine 
• 535-80-8 3-chlorobenzoate 
• 587-04-2 m-Chlorobenzaldehyde 
• 191097-25-3 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-7-methyl-3-oxo-2H-1,4-benzoxazine 

Downstream Products

• 59347-49-8 1-(3-chloro-benzyl)-pyridinium; bromide 
• 15184-97-1 1-(3-chlorophenyl)-N,N-dimethylmethanamine 
• 860585-13-3 1-(3-chloro-benzyloxy)-2-methoxy-benzene 
• 872278-13-2 (+/-)-3-(3-chloro-phenyl)-2-benzyl-propionic acid 
• 89802-75-5 3-chlorobenzyl imidothiocarbamate 
• 51229-57-3 (3-chloro-benzyl)-phenyl sulfone 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 39191-07-6 3-chloro-N-methylbenzylamine 
• 25251-56-3 (3-chloro-benzyl)-trimethyl-ammonium; bromide 
• 70450-41-8 1-chloro-3-(iodomethyl)benzene 
• 67219-34-5 2-[(3-chloro-phenyl)-methanesulfonyl]-benzothiazole 
• 67219-36-7 2-(3-chloro-benzylsulfanyl)-thiazolo[5,4-b]pyridine 
• 55614-65-8 6-Chloro-1-(4-chloro-phenyl)-3-methyl-naphthalene 
• 71570-97-3 1-Chloro-3-(2,2-dichloro-ethyl)-benzene 

Relevant academic research and scientific papers

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

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.

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature

Benzylic sp 3 C-H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO 2 Et, CO 2 H, CN or NO 2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study

A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.

Method for preparing benzyl bromide

The invention provides a method for preparing benzyl bromide. The method comprises the following steps: by taking bromine released from a redox reaction between bromates and negative bromide ions in the presence of an acid as a bromine source in an organic solvent, carrying out a benzyl radical substitution reaction with a methylbenzene compound shown as a formula I under initiation of an initiator, thereby obtaining a corresponding benzyl bromide compound shown a formula II, wherein in the formula II, m represents the number of Br and is equal to 1 or 2; when m is equal to 1, the formula II shows a benzyl monobromo compound; and when m is equal to 2, the formula II shows a benzyl dibromo compound. The reaction is carried out in an organic solvent, the initiator is combined and used, the radical substitution reaction is high in selectivity and wide in substrate application range, the substituent group replacing methylbenzene may be an electron-withdrawing group or an electron-donating group and can give extremely high yield on strong electron-donating groups (such as methoxy group). Moreover, the method disclosed by the invention is also applicable to preparation of benzyl dibromo compounds, and the product yield is high.

Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent

In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 μg/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 μg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents.

Synthesis, biological evaluation and molecular docking of novel coumarin incorporated triazoles as antitubercular, antioxidant and antimicrobial agents

A series of new coumarin-based 1,2,3-triazole derivatives were designed, synthesized and evaluated for their antitubercular activity in vitro against Mycobacterium tuberculosis H37Ra, antioxidant activity by DPPH radical scavenging assay, antimicrobial activity in vitro against three gram-positive bacteria (Staphylococcus aureus, Micrococcus luteus and Bacillus cereus) and three gram-negative bacteria (Escherichia coli, Pseudomonas fluorescens and Flavobacterium devorans as well as three fungi (Aspergillus niger, Penicillium chrysogenum and Curvularia lunata). The bioactive assay showed that some synthesized coumarin triazoles displayed comparable or even better antitubercular, antioxidant, antibacterial and antifungal efficacy in comparison with reference drugs. Furthermore, docking study has been performed against DprE1 enzyme of M. tuberculosis that showed good binding interactions. Moreover, the synthesized compounds were also analyzed for ADME properties and showed potential to build up as good oral drug candidates. Graphical Abstract: New coumarin-based 1,2,3-triazole derivatives were designed, synthesized and evaluated for their antitubercular, antioxidant, antibacterial and antifungal activity. Some of the coumarin-based triazole derivatives displayed comparable or even better efficacy in comparison with reference drugs. Molecular docking study has been performed against DprE1 enzyme of Mycobacterium tuberculosis showed good binding interactions.

1,2,3-Triazole tethered acetophenones: Synthesis, bioevaluation and molecular docking study

A small focused library of eighteen new 1,2,3-triazole tethered acetophenones has been efficiently prepared via click chemistry approach and evaluated for their antifungal and antioxidant activity. The antifungal activity was evaluated against five human pathogenic fungal strains: Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger, and Cryptococcus neoformans. Among the synthesized compounds, 9c, 9i, and 9p found to be more potent antifungal agents that the reference standard. These 1,2,3-triazole based derivatives were also evaluated for antioxidant activity, and compound 9h was found to be the most potent antioxidant as compared to the standard drug. Furthermore, molecular docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14α-demethylase. Moreover, the synthesized compounds were also analyzed for ADME properties and showed potential as good oral drug candidates.

1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents

A series of novel ethyl-7-((1-(benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-oxo-2H-chromene-3-carboxylates 8a-h as potential antifungal agents were synthesized via click chemistry. The antifungal activity was evaluated against five human pathogenic fungal strains, such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Compound 8c, 8d, 8e and 8h were found to be equipotent against C. albicans when compared with miconazole and compound 8f was found to be two-fold more active compared with miconazole and equipotent to fluconazole against C. albicans. The coumarin-based triazole derivatives were also evaluated for antioxidant activity and compound 8a was found to be potent antioxidant when compared with standard drug. Furthermore, molecular docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14α-demethylase. Moreover, the synthesized compounds were also analyzed for ADME properties and showed potential to build up as good oral drug candidates.