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 
• 67-66-3 chloroform 
• 93-61-8 N-methyl-N-phenylformamide 
• 100-97-0 hexamethylenetetramine 
• 64-19-7 acetic acid 
• 4660-96-2 N,N-dimethyl-1-(2-phenyl-1H-indol-3-yl)methanamine 
• 14300-21-1 2-phenylbenzo[d][1,3]oxazepine 
• 68-12-2 N,N-dimethyl-formamide 
• 10257-92-8 2-phenyl-3-methyl-1H-indole 
• 5659-33-6 2-phenylquinoline 1-oxide 
• 1859-39-8 2-phenyl-N-hydroxyindole 
• 20389-12-2 2-phenylquinoline 1-oxide-4-carboxylic acid 
• 32501-94-3 (ethynylsulfonyl)benzene 
• 201024-81-9 C,N-diphenylnitrone 

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.

Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes

The oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also be extended for the synthesis of aryl and other heteroaryl aldehydes and ketones. Furthermore, the usefulness of the method is successfully demonstrated on a gram scale.

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.

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020