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

Description

2-PHENYLINDOLE-3-CARBOXALDEHYDE is an organic compound that serves as a versatile intermediate in the synthesis of various pharmaceutically active molecules. It is characterized by the presence of an indole ring with a phenyl group at the 2nd position and a formyl group at the 3rd position, which allows for a wide range of chemical reactions and applications in the field of medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used as a reactant for the preparation of various bioactive compounds, making it a valuable building block in drug discovery and development.
As Tryptophan Dioxygenase Inhibitors:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used as a reactant for the synthesis of pyridyl-ethenyl-indoles, which are potential anticancer immunomodulators. These compounds can modulate the immune response and exhibit anticancer properties.
As Antimicrobial Agents:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the preparation of pyrimidinones via the Biginelli reaction. These compounds exhibit antimicrobial activity, making them useful in the development of new antibiotics.
As Antiinflammatory Agents and Analgesics:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of [(phenyl)pyrazolyl]indole derivatives, which possess antiinflammatory and analgesic properties. These compounds can be used in the treatment of inflammation and pain.
As Antimicrobial and Antioxidant Agents:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the preparation of indole thiophene chalcones via Claisen-Schmidt condensation. These chalcones exhibit both antimicrobial and antioxidant activities, making them potential candidates for use in pharmaceutical and cosmetic products.
As PI3K Inhibitors:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of benzofuranone attached indole derivatives, which act as PI3K inhibitors. These compounds can be used in the development of targeted cancer therapies.
As Novel Antiandrogens:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the preparation of ionone-based chalcones, which have been found to possess antiandrogen properties. These compounds can be used in the treatment of prostate cancer and other androgen-dependent conditions.
As Antiinflammatory Agents for Edema:
2-PHENYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of oxazolylindoles, which exhibit antiinflammatory properties and can be used in the treatment of edema and other inflammatory conditions.

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

• 948-65-2 2-phenyl-indole 
• 100-97-0 hexamethylenetetramine 
• 64-19-7 acetic acid 
• 5659-33-6 2-phenylquinoline 1-oxide 
• 20389-12-2 2-phenylquinoline 1-oxide-4-carboxylic acid 
• 32501-94-3 (ethynylsulfonyl)benzene 
• 201024-81-9 C,N-diphenylnitrone 
• 119910-45-1 2-bromo-1H-indole-3-carbaldehyde 
• 595-90-4 tetraphenyltin(IV) 
• 581783-44-0 3-(3-methyl-thiazolidin-2-yl)-2-phenyl-1H-indole 
• 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 

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 
• 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 
• 154374-24-0 3-<3-(4-fluorophenyl)-3-oxo-propene-1-yl>-2-phenyl-indole 
• 127302-27-6 1-(4-{[1-(2-Phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-ethanone 

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.

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

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.

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.