152807-26-6

Basic information

• Product Name: 3-(4'-FLUOROBENZOYL)INDOLE
• Synonyms: Methanone, (4-fluorophenyl)-1H-indol-3-yl-
• CAS NO: 152807-26-6
• Molecular Formula: C₁₅H₁₀FNO
• Molecular Weight: 239.25
• Mol File: 152807-26-6.mol

Chemical Properties

• Boiling Point: 428.655 °C at 760 mmHg
• Flash Point: 213.043 °C
• Appearance: /
• Density: 1.299 g/cm³
• Storage Temp.: 2-8°C
• PKA: 15.15±0.30(Predicted)
• CAS DataBase Reference: 3-(4'-FLUOROBENZOYL)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4'-FLUOROBENZOYL)INDOLE(152807-26-6)
• EPA Substance Registry System: 3-(4'-FLUOROBENZOYL)INDOLE(152807-26-6)

Safety Data

• Hazardous Substances Data: 152807-26-6(Hazardous Substances Data)

Usage

Uses

Used in Synthetic Chemistry:
3-(4'-Fluorobenzoyl)indole is used as a synthetic intermediate for the preparation of various complex organic molecules. Its unique molecular structure, featuring a fluorobenzoyl group and an indole ring, allows for versatile chemical reactions and modifications, making it a valuable component in the synthesis of novel compounds.
Used in Drug Discovery:
3-(4'-Fluorobenzoyl)indole is used as a potential lead compound in drug discovery. The presence of the fluorine atom and the indole ring may confer biological activity, making it a candidate for further investigation and optimization in the development of new therapeutic agents. Its potential applications in this field could include the treatment of various diseases and conditions, pending further research and validation.

Upstream product

• 120-72-9 indole 
• 403-43-0 4-fluorobenzoyl chloride 
• 1194-02-1 4-fluorobenzonitrile 
• 587-88-2 ethyl 2-(4-fluorophenyl)acetate 

Downstream Products

• 222306-42-5 (1-ethyl-1H-indol-3-yl)-(4-fluoro-phenyl)-methanone 
• 1304522-57-3 3-(4-fluorobenzoyl)-1-phenylsulfonyl-1H-indole 

Relevant articles and documents

Synthesis of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates

An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.

Synthesis of 3-aroylindoles as intermediates of cannabimimetics and elucidation of their physicochemical properties

In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the1H NMR spectra of 3-(2'-substitute

Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones

Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles

An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N-H) indoles and nitriles has been developed. The acylation reaction proceeded well under the Pd(OAc)2/2,2′-bipyridine system and with d-(+)-camphorsulfonic acid as the additive. A possible mechanism involving carbopalladation of nitriles and subsequent hydrolysis of ketimines is proposed.

New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2, 3 or 5-(α-azolylbenzyl)-1H-indoles

Six azolyl substituted indoles were synthesized and tested for their activity to inhibit two P450 enzymes: P450 arom and P450 17α. It was observed that the introduction of α-imidazolylbenzyl chain at carbon 3 or 5 on indole nucleus led to very active molecules. Compounds 22, 23 and especially 33 demonstrate very high potential against P450 arom. Under our assay conditions of high substrate concentration the IC50 are 0.057, 0.0785 and 0.041 μM, respectively. These compounds are moderate inhibitors against P450 17α.

The use of Lewis acid in the reaction of zinc salts of indoles and acyl chloride

3-Acylindoles have been prepared in 62 - 92% isolated yield from the corresponding indoles and acyl chlorides in the presence of AlCl3.