101125-32-0

Basic information

• Product Name: 3-(4-FLUORO-PHENYL)-1H-INDOLE
• Synonyms: 3-(4-FLUORO-PHENYL)-1H-INDOLE;3-(4-FLUOROPHENYL)-INDOLE;3-(4-Fluoro-phenyl)-1H-indole hydrochloride;1H-Indole, 3-(4-fluorophenyl)-
• CAS NO: 101125-32-0
• Molecular Formula: C₁₄H₁₀FN
• Molecular Weight: 211.23
• Mol File: 101125-32-0.mol

Chemical Properties

• Melting Point: 96-98 °C
• Boiling Point: 390.511 °C at 760 mmHg
• Flash Point: 189.974 °C
• Appearance: /
• Density: 1.233 g/cm³
• Vapor Pressure: 5.93E-06mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 16.49±0.30(Predicted)
• CAS DataBase Reference: 3-(4-FLUORO-PHENYL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-FLUORO-PHENYL)-1H-INDOLE(101125-32-0)
• EPA Substance Registry System: 3-(4-FLUORO-PHENYL)-1H-INDOLE(101125-32-0)

Safety Data

• Hazardous Substances Data: 101125-32-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-FLUORO-PHENYL)-1H-INDOLE is used as a reagent for the synthesis of indole-based sigma receptor ligands, which are important in the development of drugs targeting the sigma receptors. These ligands have potential applications in the treatment of various neurological and psychiatric disorders, as well as in the development of analgesics and anti-inflammatory agents.
Used in the Synthesis of Fluvastatin (F601250):
3-(4-FLUORO-PHENYL)-1H-INDOLE is also utilized in the preparation of Fluvastatin (F601250), a synthetic HMG-CoA reductase inhibitor. 3-(4-FLUORO-PHENYL)-1H-INDOLE is widely used in the treatment of hypercholesterolemia and other lipid disorders, as it helps to lower the levels of low-density lipoprotein (LDL) cholesterol in the blood, thereby reducing the risk of cardiovascular diseases.
Used as an Antilipemic:
In addition to its role in the synthesis of sigma receptor ligands and Fluvastatin, 3-(4-FLUORO-PHENYL)-1H-INDOLE is also used as an antilipemic agent. It helps to regulate lipid metabolism and maintain healthy blood lipid levels, which is essential for the prevention and management of various cardiovascular and metabolic disorders.

InChI:InChI=1/C14H10FN/c15-11-7-5-10(6-8-11)13-9-16-14-4-2-1-3-12(13)14/h1-9,16H

Upstream product

• 31681-99-9 1-(4-fluorophenyl)-2-(phenylamino)ethanone 
• 141306-66-3 3-(4-fluorophenyl)-1H-indole-2-carboxylic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 143360-93-4 N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide 
• 122255-02-1 methyl 2-(4-fluorobenzyl)-3-oxobutanoate 
• 141306-65-2 methyl 3-(4-fluorophenyl)-1H-indole-2-carboxylate 
• 1477-50-5 Indole-2-carboxylic acid 
• 120-72-9 indole 
• 1038997-83-9 (4-fluorophenyl)(2,4,6-triisopropylphenyl)iodonium triflate 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 98-95-3 nitrobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 1340592-97-3 3-(4-fluorophenyl)-1-(phenylsulfonyl)indole 
• 99655-68-2 3-bromo-1-phenylsulfonyl indole 

Downstream Products

• 1340592-99-5 1-(4-bromobutyl)-3-(4-fluorophenyl)indole 
• 1121931-22-3 1-(4-(4-cyclohexylpiperazin-1-yl)butyl)-3-(4-fluorophenyl)indole 
• 1121931-25-6 3-(4-fluorophenyl)-1-(4-(4-(4-fluorophenyl)piperazin-1-yl)butyl)indole 
• 1121931-42-7 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 93957-49-4 3-(4'-fluorophenyl)-1-(1'-methylethyl)-1H-indole 
• 129332-30-5 3-(3-(4-fluorophenyl)-1-iso propyl-1H-indol-2-yl)Acrolein 

Relevant articles and documents

Structure Ligation Relationship of Amino Acids for the Selective Indole C?H Arylation Reaction: L-Aspartic acid as Sustainable Alternative of Phosphine Ligands

The Structure Ligation Relationship (SLR) of free amino acids (AAs) under Pd-catalysis were examined for the chemo- and regio-selective indole C?H arylation reactions. While the majority of AAs were minor or ineffective, the L-aspartic acid (L-Asp) stands out promising to deliver high-value C3-arylated indoles with excellent chemo- (C vs N) and regioselectivity (C3 vs C2) with high functional group tolerance. Thus, the protocol offers a cost-effective and sustainable alternative of phosphine-based ligands for the indole C3?H arylation reactions. Preliminary mechanistic investigations suggested the simultaneous involvement of ?NH2, α-CO2H, and β-CO2H functionalities of L-Asp and found critical for its ligation efficiency. The developed catalytic system was compatible with the tandem decarboxylation/arylation procedure for the chemoselective synthesis of 3-aryl indoles. (Figure presented.).

Atom-economical transformation of diaryliodonium salts: Tandem C-H and N-H arylation of indoles

Arylation using diaryliodonium salts generates one equivalent of an iodoarene as a side-product, a significant waste of atom economy. Here, we show that diaryliodoniums can undergo Cu-catalyzed tandem C-H/N-H arylation, producing novel indoles that incorporate both aryl groups from the reagent.

A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water

The selective control over multiple competing C-H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C-H arylation of indoles following the micellar catalysis approach using the third generation "designer" surfactant SPGS-550-M in the presence of 1 mol% of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the "triple bottom line philosophy" of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.

Pyridylmethylamine–Palladium Catalytic Systems: A Selective Alternative in the C?H Arylation of Indole

A highly efficient pyridylmethylamine-Pd alternative catalytic system for the C?H arylation of indole was explored. Variously substituted aryl groups were regio- and chemoselectively installed at the indole nucleus by using barium hydroxide as the base. The method was found to be efficient even in the presence of hindered coupling partners and Pd-reactive bonds.

Synthesis of indoles by intermolecular cyclization of unfunctionalized nitroarenes and alkynes: one-step synthesis of the skeleton of fluvastatin

The addition of Ru3(CO)12, dimethyl carbonate, or both to the reaction mixture improves the selectivity of the palladium/phenanthroline-catalyzed reaction of nitroarenes, arylalkynes, and CO to give 3-arylindoles. When 4-fluorophenyl

Synthesis and antimycobacterial activity of 3-phenyl-1h-indoles

Tuberculosis has been described as a global health crisis since the 1990s, with an estimated 1.4 million deaths in the last year. Herein, a series of 20 1H-indoles were synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (Mtb) g

Direct C3-Selective Arylation of N-Unsubstituted Indoles with Aryl Chlorides, Triflates, and Nonaflates Using a Palladium-Dihydroxyterphenylphosphine Catalyst

A palladium-dihydroxyterphenylphosphine (DHTP) catalyst was successfully applied to the direct C3-arylation of N-unsubstituted indoles with aryl chlorides, triflates, and nonaflates. This catalyst showed C3-selectivity, whereas catalysts with other structurally related ligands exhibited N1-selectivity. Complex formation between the lithium salts of the ligand and the indole is assumed to accelerate the arylation at the C3 position. Reactions using 3-alkylindoles afforded 3,3-disubstituted indolenines, which can be further converted to the corresponding indoline derivatives.

Metal-free and regiospecific synthesis of 3-arylindoles

A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate

Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.