255724-72-2

Basic information

• Product Name: 1H-INDOLE, 6-FLUORO-2-PHENYL-
• Synonyms: 1H-INDOLE, 6-FLUORO-2-PHENYL-;6-FLUORO-2-PHENYL-1H-INDOLE
• CAS NO: 255724-72-2
• Molecular Formula: C₁₄H₁₀FN
• Molecular Weight: 211.238
• Mol File: 255724-72-2.mol

Chemical Properties

• Melting Point: 171-172℃
• Boiling Point: 395.755°C at 760 mmHg
• Flash Point: 193.146°C
• Appearance: /
• Density: 1.233g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-INDOLE, 6-FLUORO-2-PHENYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE, 6-FLUORO-2-PHENYL-(255724-72-2)
• EPA Substance Registry System: 1H-INDOLE, 6-FLUORO-2-PHENYL-(255724-72-2)

Safety Data

• Hazardous Substances Data: 255724-72-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1H-Indole, 6-fluoro-2-phenylis used as a building block in the creation of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with potential applications in these fields.
Used in Medicinal Chemistry:
1H-Indole, 6-fluoro-2-phenylis used as a potential candidate in medicinal chemistry due to its unique structure and the presence of a fluorine atom. This makes it a subject of interest for further research and exploration, with the aim of discovering new therapeutic agents.
Used in Drug Development:
1H-Indole, 6-fluoro-2-phenyl-'s unique structure and potential biological activities make it a valuable asset in drug development. Its use in this field can lead to the creation of new drugs with improved efficacy and selectivity.

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

Upstream product

• 1027976-96-0 5-fluoro-2-phenylethynylphenylamine 
• 863870-42-2 2-(2,2-dibromo-vinyl)-5-fluoro-phenylamine 
• 98-80-6 phenylboronic acid 
• 2923-96-8 4-fluoro-2-nitrobenzaldehyde 
• 446-09-3 2-bromo-5-fluoronitrobenzene 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 255724-71-1 5-fluoro-2-iodoaniline 
• 1037492-79-7 4-fluoro-2-nitro-1-(phenylethynyl)benzene 
• 1314247-87-4 2-bromo-4-fluoro-1-(phenylethynyl)benzene 
• 399-51-9 6-fluoro-1H-indole 
• 618-41-7 Benzenesulfinic acid 
• 873-55-2 sodium benzenesulfonate 
• 1552279-98-7 (E)-1-((5-fluoro-2-iodophenyl)diazenyl)piperidine 

Downstream Products

• 342902-37-8 4-(6-fluoro-2-phenyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 342902-38-9 (3S,4S)-4-(6-Fluoro-2-phenyl-1H-indol-3-yl)-3-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 1262876-51-6 Methyl 6-(6-fluoro-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate 
• 1315337-24-6 7-fluoro-2-phenylquinazolin-4(3Η)-one 

Relevant articles and documents

Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones

A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.

INHIBITORS OF APOL1 AND METHODS OF USING SAME

The disclosure provides at least one entity chosen from compounds of formula (I), solid state forms of the same, compositions comprising the same, and methods of using the same, including use in treating focal segmental glomerulosclerosis (FSGS) and/or non-diabetic kidney disease (NDKD).

Well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes-catalyzed direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides

A series of well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes (N–heterocyclic carboxylate = pyridine-2-carboxylate, quinoline-2-carboxylate and isoquinoline-1-carboxylate) were synthesized and fully characterized by NMR spectra, HR-MS and X-ray single crystal diffraction. The obtained complexes were then used for direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides. With low catalyst loading, all complexes exhibited high catalytic activities for the arylation reactions.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones

A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.

Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.

Application of Fluorine- And Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators

Cannabinoid 1 receptor (CB1R) allosteric ligands hold a far-reaching therapeutic promise. We report the application of fluoro- and nitrogen-walk approaches to enhance the drug-like properties of GAT211, a prototype CB1R allosteric agonist-positive allosteric modulator (ago-PAM). Several analogs exhibited improved functional potency (cAMP, β-arrestin 2), metabolic stability, and aqueous solubility. Two key analogs, GAT591 (6r) and GAT593 (6s), exhibited augmented allosteric-agonist and PAM activities in neuronal cultures, improved metabolic stability, and enhanced orthosteric agonist binding (CP55,940). Both analogs also exhibited good analgesic potency in the CFA inflammatory-pain model with longer duration of action over GAT211 while being devoid of adverse cannabimimetic effects. Another analog, GAT592 (9j), exhibited moderate ago-PAM potency and improved aqueous solubility with therapeutic reduction of intraocular pressure in murine glaucoma models. The SAR findings and the enhanced allosteric activity in this class of allosteric modulators were accounted for in our recently developed computational model for CB1R allosteric activation and positive allosteric modulation.

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.

Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines

A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.

Synthetic method of 2-substituted indoles compounds

The invention discloses a synthetic method of 2-substituted indoles compounds, and belongs to the organic synthesis field. 2-fluorotoluene compound shown in formula 1 and nitrile compound shown in formula 2 mix with an organic solvent in the presence of strong alkali and cesium salt additives, and react to synthesize the 2-substituted indoles compounds shown in formula 3. The synthesis method of 2-substituted indoles compounds is simple, economical and has wider applicability, is suitable for large-scale production, and has a very important influence on the synthesis of indoles compounds.