54031-95-7

Basic information

• Product Name: 2-(4-BROMOPHENYL)-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 2-(4-BROMOPHENYL)-1H-INDOLE-3-CARBALDEHYDE
• CAS NO: 54031-95-7
• Molecular Formula: C₁₅H₁₀BrNO
• Molecular Weight: 300.15
• Mol File: 54031-95-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-BROMOPHENYL)-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMOPHENYL)-1H-INDOLE-3-CARBALDEHYDE(54031-95-7)
• EPA Substance Registry System: 2-(4-BROMOPHENYL)-1H-INDOLE-3-CARBALDEHYDE(54031-95-7)

Safety Data

• Hazardous Substances Data: 54031-95-7(Hazardous Substances Data)

Usage

Description

2-(4-Bromophenyl)-1H-indole-3-carbaldehyde is a chemical compound characterized by a molecular formula of C14H10BrNO. It features a benzene ring with a bromine atom substitution, which is connected to an indole ring. The indole ring has a carbonyl group attached to the third carbon, endowing the compound with aldehyde functionality. This unique structure and its reactive properties make it a significant building block in the synthesis of a variety of organic compounds, particularly in the fields of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
2-(4-Bromophenyl)-1H-indole-3-carbaldehyde is used as a reagent and intermediate in the synthesis of pharmaceuticals. Its aldehyde group allows for various chemical reactions, facilitating the creation of new drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(4-Bromophenyl)-1H-indole-3-carbaldehyde is utilized as a precursor in the development of new agrochemicals. Its unique structure can be modified to produce compounds with pesticidal or herbicidal properties, contributing to the advancement of crop protection strategies.
Used in Organic Synthesis:
2-(4-Bromophenyl)-1H-indole-3-carbaldehyde is employed as a key intermediate in organic synthesis. Its reactive aldehyde group and the presence of a bromine atom on the benzene ring make it a versatile building block for the creation of diverse organic compounds, which can be further utilized in various chemical research and manufacturing processes.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 6127-49-7 2-(4-bromophenyl)indole 
• 99-90-1 para-bromoacetophenone 
• 100-63-0 phenylhydrazine 
• 10591-75-0 4-bromoacetophenone phenylhydrazone 

Downstream Products

• 76699-15-5 (E)-3-[2-(4-Bromo-phenyl)-1H-indol-3-yl]-1-(4-chloro-phenyl)-propenone 
• 76699-14-4 (E)-3-[2-(4-Bromo-phenyl)-1H-indol-3-yl]-1-(4-nitro-phenyl)-propenone 
• 71491-11-7 2-(4-Bromo-phenyl)-3-[5-(4-chloro-phenyl)-2-(2,4-dinitro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-1H-indole 
• 1351939-89-3 2-amino-4-(2-(4-bromophenyl)-1H-indol-3-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1351939-90-6 2-amino-4-(2-(4-bromophenyl)-1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 

Relevant articles and documents

Discovery of novel multi-substituted benzo-indole pyrazole schiff base derivatives with antibacterial activity targeting DNA gyrase

The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, we selected 20 compounds for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound 8I-w exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC50 values of 7.0, 17.0, 13.5, and 1.0 μM, respectively. In vitro enzyme inhibitory assay showed that compound 8I-w displayed potent inhibition against DNA gyrase with IC50 values of 0.10 μM. The molecular docking model indicated that compounds 8I-w can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound 8I-w can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.

Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study

In this work, two novel series of indole-thiosemicarbazone derivatives were designed, synthesized, and evaluated for their cytotoxic activity against MCF-7, A-549, and Hep-G2 cell lines in comparison to etoposide and colchicine as the reference drugs. Generally, the synthesized compounds showed better cytotoxicity towards A-549 and Hep-G2 than MCF-7. Among them, (2E)-2-{[2-(4-chlorophenyl)-1H-indol-3-yl]methylidene}-N-(4-methoxyphenyl)hydrazinecarbothioamide (8l) was found to be the most potent compound against A-549 and Hep-G2, at least three times more potent than etoposide. The morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that compound 8l induced apoptosis in A-549 cells. Moreover, molecular docking methodology was exploited to elucidate the details of molecular interactions of the studied compounds with putative targets.

Green approach for the synthesis of 3-methyl-1-phenyl-4-((2-phenyl-1H-indol 3-yl)methylene)-1H-pyrazole-5(4H)-ones and their DNA Cleavage, antioxidant, and antimicrobial activities

3-Methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones (5a-i) was prepared by the condensation reaction of different 3-formyl-2-phenylindole derivatives (2a-i) and 3-methyl-1-phenyl-2-pyrazoline-5-one in quantitative yield by applying various green synthetic methods as grinding, microwave irradiation using different catalysts under solvent-free mild reaction conditions with high product yields. The structures of the synthesized compounds were characterized on the basis of elemental analysis, infrared, 1HNMR, 13C NMR, and mass spectral data. The synthesized compounds were screened for free radical scavenging, antimicrobial, and DNA cleavage activities. Most of the tested compounds belonging to the 3-methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones series exhibited promising activities.