25365-71-3

Basic information

• Product Name: 2-PHENYLINDOLE-3-CARBOXALDEHYDE
• Synonyms: OTAVA-BB BB7214110035;AURORA 23280;ART-CHEM-BB B023284;2-PHENYLINDOLE-3-ALDEHYDE;2-PHENYLINDOLE-3-CARBOXALDEHYDE;2-PHENYL-1H-INDOLE-3-CARBALDEHYDE;3-FORMYL-2-PHENYL-INDOLE;AKOS SVR00140
• CAS NO: 25365-71-3
• Molecular Formula: C₁₅H₁₁NO
• Molecular Weight: 221.25
• Product Categories: Indoles and derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 25365-71-3.mol
• Article Data: 55

Chemical Properties

• Melting Point: 249-253 °C(lit.)
• Boiling Point: 462.9 °C at 760 mmHg
• Flash Point: 237.5 °C
• Appearance: /
• Density: 1.237 g/cm³
• Vapor Pressure: 9.47E-09mmHg at 25°C
• Refractive Index: 1.709
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 15.30±0.30(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-PHENYLINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLINDOLE-3-CARBOXALDEHYDE(25365-71-3)
• EPA Substance Registry System: 2-PHENYLINDOLE-3-CARBOXALDEHYDE(25365-71-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 25365-71-3(Hazardous Substances Data)

Usage

Uses

Reactant for preparation of: Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsPyrimidinones via Biginelli reaction as antimicrobial agents[(phenyl)pyrazolyl]indole derivatives as antiinflammatory agents and analgesicsIndole thiophene chalcones via Claisen-Schmidt condensation as antimicrobial and antioxidant agentsBenzofuranone attached indole derivatives as PI3K inhibitorsIonone-based chalcones as novel antiandrogensOxazolylindoles as antiinflammatory agents for edema

InChI:InChI=1/C15H11NO/c17-10-13-12-8-4-5-9-14(12)16-15(13)11-6-2-1-3-7-11/h1-10,16H

Upstream product

• 14300-21-1 2-phenylbenzo[d][1,3]oxazepine 
• 20389-12-2 2-phenylquinoline 1-oxide-4-carboxylic acid 
• 32501-94-3 (ethynylsulfonyl)benzene 
• 201024-81-9 C,N-diphenylnitrone 
• 948-65-2 2-phenyl-indole 
• 298-12-4 Glyoxilic acid 
• 93-61-8 N-methyl-N-phenylformamide 
• 67-66-3 chloroform 
• 4660-96-2 N,N-dimethyl-1-(2-phenyl-1H-indol-3-yl)methanamine 
• 59-48-3 2-oxoindole 
• 5059-30-3 2-chloroindole-3-carboxaldehyde 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 62-53-3 aniline 

Downstream Products

• 67522-88-7 1-Ethyl-2-phenylindole-3-carboxaldehyde 
• 41450-77-5 3-(3-formyl-2-phenyl-indol-1-yl)-propionitrile 
• 120607-72-9 ethyl (2E)-2-cyano-3-(2-phenyl-1H-indol-3-yl)acrylate 
• 136230-34-7 3t-(2-phenyl-indol-3-yl)-1-p-tolyl-propenone 
• 1757-72-8 1-methyl-2-phenyl-1H-indole-3-carbaldehyde 
• 76869-07-3 (2-phenyl-1H-indol-3-yl)methanol 
• 150391-49-4 2-Methyl-3-{[1-(2-phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-3H-quinazolin-4-one 
• 82327-13-7 (4-Morpholin-4-yl-phenyl)-[1-(2-phenyl-1H-indol-3-yl)-meth-(Z)-ylidene]-amine 
• 151390-85-1 (E)-1-(2-Nitro-phenyl)-3-(2-phenyl-1H-indol-3-yl)-propenone 
• 122631-45-2 (E)-3-(2-methyl-2-nitrovinyl)-2-phenyl-1H-indole 
• 122631-43-0 (E)-3-(2-nitrovinyl)-2-phenyl-1H-indole 
• 154374-25-1 (E)-1-(4-Fluoro-2-methyl-phenyl)-3-(2-phenyl-1H-indol-3-yl)-propenone 
• 126479-65-0 N,N-Diphenyl-4-{[1-(2-phenyl-1H-indol-3-yl)-meth-(Z)-ylidene]-amino}-benzamide 
• 156385-97-6 1-acetyl-2-phenyl-1H-indole-3-carbaldehyde 

Relevant articles and documents

An Efficient, Eco-Friendly Synthesis of Pyran Annulated Indole Analogs under Conventional Heating and Microwave Irradiation, and Their Anticancer and Antioxidant Activity

A rapid, facile, green, eco-friendly, cost effective, and efficient method for the synthesis of pyran annulated indole analogs via one-pot, three components reaction is developed. According to the developed method 2,5-disubstituted-1H-indol-3-carboxaldehyde, malononitrile and various phenols react under MW assisted solvent-free conditions. These compounds can be also prepared under a conventional method that is characterized by some disadvantages in comparison with the above approach. Structures of products are confirmed by FT-IR, 1H and 13C NMR, and mass spectral data. The in vitro antioxidant and cytotoxic activities of the products are evaluated against three tumor cell lines and discussed in terms of structure―activity analysis. Among the screened compounds 3d, 4a, 4b, 5a, and 5b exhibit excellent antioxidant activity. Compounds 4b, 5a, and 5b demonstrate strong cytotoxic activity.

C3-Formylation of Indoles in Continuous Flow

We have developed a continuous flow C3-formylation technique for indoles using hexamethylenetetramine (HMTA) and iodine. A mixed solvent system of DMF–H2O (1:1, vol/vol) completely dissolves reagents and prevents clogging of microchannels during fluid flow. The continuous flow technique provides maximized mixing and excellent heat transfer efficiency. Thus, flow chemistry accelerates the rate of C3-formylation of indoles in the absence of a strong acid, base, or metal catalyst. We show that high yields of C3-formylated indoles (up to 83%) can be obtained at 150°C when the residence time is as low as 8 min.

Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis

There are several potential side and adverse effects are found to be associated with the anti-inflammatory drugs in clinical practice. The long-term use of these clinical agents highly unsafe. It encouraged the development of novel heterocyclic compounds with potential anti-inflammatory activity and low to no toxicity. In present investigation, a total of 12 indole functionalized pyrazole and oxadiazole derivatives were designed, synthesized and evaluated for the in-vivo anti-inflammatory and analgesic potential. These compounds displayed comparable anti-inflammatory and analgesic potential to the reference drugs. Finally, molecular docking analysis was performed considering different anti-inflammatory targets to determine the mechanistic target of the designed molecules. Detailed analysis suggested that the molecules inhibit COX-2, preferably over other anti-inflammatory targets. The results suggested that two compounds (15c and 15f) were found promising candidates for the development of novel anti-inflammatory agents.

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.