13228-36-9

Basic information

• Product Name: 5-METHYL-2-PHENYLINDOLE
• Synonyms: 1H-INDOLE, 5-METHYL-2-PHENYL-;5-METHYL-2-PHENYL-1H-INDOLE;5-METHYL-2-PHENYLINDOLE;5-METHYL-2-PHENYLINDOLE, 97% MIN.;(5-Methyl-1H-indol-2-yl)benzene
• CAS NO: 13228-36-9
• Molecular Formula: C₁₅H₁₃N
• Molecular Weight: 207.27
• Mol File: 13228-36-9.mol
• Article Data: 88

Chemical Properties

• Melting Point: 214-215 °C
• Boiling Point: 404.2 °C at 760 mmHg
• Flash Point: 180.7 °C
• Appearance: /
• Density: 1.129 g/cm³
• Vapor Pressure: 2.25E-06mmHg at 25°C
• Refractive Index: 1.662
• PKA: 16.97±0.30(Predicted)
• CAS DataBase Reference: 5-METHYL-2-PHENYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-2-PHENYLINDOLE(13228-36-9)
• EPA Substance Registry System: 5-METHYL-2-PHENYLINDOLE(13228-36-9)

Safety Data

• Hazardous Substances Data: 13228-36-9(Hazardous Substances Data)

Usage

General Description

5-Methyl-2-phenylindole is a chemical compound that contains a methyl group and a phenyl group attached to a central indole ring structure. It is commonly used in the synthesis of various pharmaceuticals and organic compounds due to its unique structural features and reactivity. The presence of the indole ring makes it an important building block in the production of many biologically active molecules, while the methyl and phenyl groups add to its versatility in chemical reactions. 5-METHYL-2-PHENYLINDOLE has applications in medicinal chemistry, material science, and organic synthesis, making it a valuable tool in scientific research and development.

InChI:InChI=1/C15H13N/c1-11-7-8-14-13(9-11)10-15(16-14)12-5-3-2-4-6-12/h2-10,16H,1H3

Upstream product

• 4831-18-9 N-phenacyl-p-toluidine 
• 62-53-3 aniline 
• 93-89-0 benzoic acid ethyl ester 
• 109463-71-0 N-TMS-2,4-Dimethylaniline 
• 104683-04-7 1-(5-methyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 583-68-6 2-bromo-p-toluidine 
• 14990-66-0 1-(1-phenylvinyl)piperidine 
• 13141-44-1 4-methyl-2-(phenylethynyl)aniline 
• 623-47-2 propynoic acid ethyl ester 
• 1131890-84-0 1-tert-butyl-5-methyl-2-phenyl-1H-indole 
• 1189783-28-5 1-chloromethyl-5-methyl-2-isocyanobenzene 
• 591-51-5 phenyllithium 
• 98-86-2 acetophenone 
• 91192-26-6 2-(5-methyl-2-nitrophenyl)acetonitrile 

Downstream Products

• 132554-35-9 N-methyl-2-phenyl-5-methylindole 
• 23746-97-6 5-methyl-2-phenyl-indol-3-one oxime 
• 59490-95-8 2-benzamido-5-methylbenzoic acid 
• 23751-25-9 5-methyl-2-phenyl-indol-3-one 
• 1331947-76-2 5-methyl-1-nitroso-2-phenylindoline 
• 1331947-77-3 5-methyl-2-phenyl-N-(propan-2-ylidene)indolin-1-amine 
• 1331944-17-2 C₂₁H₂₂N₂ 
• 1416038-47-5 4-((1H-indol-3-yl)(5-methyl-2-phenyl-1H-indol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 1416038-40-8 4-(bis(5-methyl-2-phenyl-1H-indol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 1416038-41-9 4-((5-chloro-2-phenyl-1H-indol-3-yl)(5-methyl-2-phenyl-1H-indol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 1416038-42-0 4-((5-methoxy-2-phenyl-1H-indol-3-yl)(5-methyl-2-phenyl-1H-indol-3-yl)methyl)-3-methyl-1H-pyrazol-5(4H)-one 
• 1416038-43-1 3-methyl-4-((5-methyl-2-phenyl-1H-indol-3-yl)(2-phenyl-1H-indol-3-yl)methyl)-1H-pyrazol-5(4H)-one 
• 1610423-37-4 C₂₂H₂₆N₂O₂ 
• 73108-78-8 6-methyl-3-phenylquinolin-2(1H)-one 

Relevant articles and documents

Iron-palladium association in the preparation of indoles and one-pot synthesis of bis(indolyl)methanes

Indoles were prepared by annulation of the parent alkynylanilines with the use of a new FeCl3-PdCl2 catalytic combination. High yields were obtained by using low loadings of the transition-metal complex (FeCl3-PdCl2: 2 and 1 mol-%, respectively). One-pot accesses to bis(indolyl)methanes and trisubstituted indoles through annulation/Friedel-Crafts alkylation and annulation/1,4-Michael addition sequences, in which FeCl3 acts both as a cooxidant and a Lewis acid are described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Characterization of heterogeneous aryl-Pd(ii)-oxo clusters as active species for C-H arylation

C-H arylation with heterogeneous palladium was investigated. The surface oxidation of Pd nanoparticles with a hypervalent iodine reagent, [Ph2I]BF4, resulted in the generation of Pd(ii)-aryl-oxo clusters, which were characterized as the crucial intermediate.

One-pot 2-aryl/vinylindole synthesis consisting of a ruthenium-catalyzed hydroamination and a palladium-catalyzed heck reaction using 2-chloroaniline

A one-pot synthesis of 2-aryl- and 2-vinylindoles based on a ruthenium-catalyzed hydroamination and a palladium-catalyzed intramolecular Heck reaction is reported. The ruthenium-catalyzed addition reaction was applied to terminal as well as internal alkynes. Intramolecular Heck reactions of the resulting 2-chloroanilino enamines were achieved using an in situ generated palladium complex derived from an N-heterocyclic carbene. Georg Thieme Verlag Stuttgart.

InBr3-catalyzed intramolecular cyclization of 2-alkynylanilines leading to polysubstituted indole and its application to one-pot synthesis of an amino acid precursor

We describe InBr3-catalyzed cyclization of 2-alkynylaniline derivatives having a variety of functional groups producing polysubstituted indoles. This methodology could be applied to the one-pot synthesis of an amino acid precursor by the addition of a catalytic amount of the indium salt, an imine, and TMSCl.

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.).

Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.

Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides

A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.