66354-67-4

Basic information

• Product Name: 1H-INDOLE, 4-METHYL-2-PHENYL-
• Synonyms: 1H-INDOLE, 4-METHYL-2-PHENYL-;4-METHYL-2-PHENYL-1H-INDOLE
• CAS NO: 66354-67-4
• Molecular Formula: C₁₅H₁₃N
• Molecular Weight: 207.275
• Mol File: 66354-67-4.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-INDOLE, 4-METHYL-2-PHENYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE, 4-METHYL-2-PHENYL-(66354-67-4)
• EPA Substance Registry System: 1H-INDOLE, 4-METHYL-2-PHENYL-(66354-67-4)

Safety Data

• Hazardous Substances Data: 66354-67-4(Hazardous Substances Data)

Usage

Class of compound

Indoles (organic compounds)

Structure

Bicyclic heterocycles consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring

Characterizing groups

A methyl group and a phenyl group attached to the indole ring

Usage

Synthesis of pharmaceuticals, agrochemicals, and dyes; found in certain natural products

Biological activities

Anti-inflammatory, antimicrobial, and antiviral effects

Potential medicinal properties

Studied for its various biological activities and applications in the fields of chemistry and medicine

Upstream product

• 3096-94-4 N-(2,3-dimethylphenyl)benzamide 
• 863870-39-7 2-(2,2-dibromovinyl)-3-methyl-phenylamine 
• 98-80-6 phenylboronic acid 
• 29027-17-6 2-chloro-3-methylaniline 
• 98-86-2 acetophenone 
• 107096-52-6 2-methyl-6-nitrobenzaldehyde 
• 41085-43-2 2-bromo-3-nitrotoluene 
• 16096-32-5 4-methyl-1H-indole 
• 54879-20-8 2-bromo-3-methylaniline 
• 1608124-68-0 4-methyl-2-phenyl-1-(pyrimidin-2-yl)-1H-indole 
• 1427670-00-5 4-methyl-1-(pyrimidin-2-yl)-1H-indole 
• 2996-92-1 phenyl trimethylsiloxane 
• 100-42-5 styrene 
• 591-50-4 iodobenzene 

Downstream Products

• 1363261-30-6 (S)-N(α)-acetyl-4-methyl-2-phenyltryptophan methyl ester 
• 1610423-38-5 C₂₂H₂₆N₂O₂ 
• 1610423-23-8 C₁₇H₁₅NO₂ 
• 1610423-47-6 C₁₇H₁₇NO 

Relevant articles and documents

One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones

A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).

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.