144104-46-1

Basic information

• Product Name: 5-(4-METHOXY-PHENYL)-1H-INDOLE
• Synonyms: 5-(4-METHOXY-PHENYL)-1H-INDOLE;AKOS BAR-0447;5-(4-Methoxyphenyl)indole
• CAS NO: 144104-46-1
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.27
• Mol File: 144104-46-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 425.1°C at 760 mmHg
• Flash Point: 153.4°C
• Appearance: /
• Density: 1.167g/cm³
• Vapor Pressure: 4.88E-07mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 5-(4-METHOXY-PHENYL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-METHOXY-PHENYL)-1H-INDOLE(144104-46-1)
• EPA Substance Registry System: 5-(4-METHOXY-PHENYL)-1H-INDOLE(144104-46-1)

Safety Data

• Hazardous Substances Data: 144104-46-1(Hazardous Substances Data)

Usage

General Description

5-(4-Methoxy-phenyl)-1H-indole, also known as 4-Methyl-5-methoxyindole, is a chemical compound with the molecular formula C15H13NO. It is an indole derivative with a methoxy group attached to the 4th position of the phenyl ring. 5-(4-METHOXY-PHENYL)-1H-INDOLE is commonly used in organic synthesis and pharmaceutical research due to its potential pharmacological properties. It has been studied for its potential therapeutic applications, including its role in treating various medical conditions such as inflammation, cancer, and psychiatric disorders. Additionally, 5-(4-Methoxy-phenyl)-1H-indole may also have applications in the development of new drugs and medications.

InChI:InChI=1/C15H13NO/c1-17-14-5-2-11(3-6-14)12-4-7-15-13(10-12)8-9-16-15/h2-10,16H,1H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 144104-59-6 1H-indole-5-boronic acid 
• 10075-50-0 5-bromo-1H-indole 
• 5720-07-0 4-methoxyphenylboronic acid 
• 623-12-1 4-chloromethoxybenzene 
• 317830-84-5 (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid 
• 696-62-8 para-iodoanisole 
• 75400-67-8 indole-1-carboxylic acid tert-butyl ester 
• 69519-11-5 2-(4-methoxyphenyl)-[1,3,2]-dioxaborolane 
• 16066-91-4 5-iodo-1H-indole 

Downstream Products

• 1418136-25-0 2-bromo-5-(4-methoxyphenyl)-1H-indole 
• 1396300-32-5 10-(4-methoxyphenyl)-6-(4-phenoxyphenyl)indolo[2,1-a]isoquinoline 
• 1396300-29-0 6-(3-methoxyphenyl)-10-(4-methoxyphenyl)indolo[2,1-a]isoquinoline 
• 1396300-21-2 6-(biphenyl-4-yl)-10-(4-methoxyphenyl)indolo[2,1-a]isoquinoline 
• 1396300-18-7 6-(4-butylphenyl)-10-(4-methoxyphenyl)indolo[2,1-a]isoquinoline 
• 1396300-25-6 6-(4-ethylphenyl)-10-(4-methoxyphenyl)indolo[2,1-a]isoquinoline 
• 1396300-15-4 10-(4-methoxyphenyl)-6-p-tolylindolo[2,1-a]isoquinoline 

Relevant articles and documents

Cp?Co(III)-Catalyzed enantioselective hydroarylation of unactivated terminal alkenes via C-H activation

Enantioselective hydroarylation of unactivated terminal akenes constitutes a prominent challenge in organic chemistry. Herein, we reported a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by a new type of tailor-made amino acid ligands. Critical to the chiral induction was the engaging of a novel noncovalent interaction (NCI), which has seldomly been disclosed in the C-H activation area, arising from the molecular recognition among the organocobalt(III) intermediate, the coordinated alkene, and the well-designed chiral ligand. A broad range of C2-alkylated indoles were obtained in high yields and excellent enantioselectivities. DFT calculations revealed the reaction mechanism and elucidated the origins of chiral induction in the stereodetermining alkene insertion step.

Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4

Despite recent advancements in metal-catalyzed borylations of aryl (pseudo)halides, there is a continuing need to develop robust methods to access both early-stage and late-stage organoboron intermediates amendable for further functionalization. In particular, the development of general catalytic systems that operate under mild reaction conditions across a broad range of electrophilic partners remains elusive. Herein, we report the development and application of three catalytic systems (two Pd-based and one Ni-based) for the direct borylation of aryl (pseudo)halides using tetrahydroxydiboron (B2(OH)4). For the Pd-based catalyst systems, we have identified general reaction conditions that allow for the sequestration of halide ions through simple precipitation that results in catalyst loadings as low as 0.01 mol % (100 ppm) and reaction temperatures as low as room temperature. We also describe a complementary Ni-based catalyst system that employs simple unligated Ni(II) salts as an inexpensive alternative to the Pd-based systems for the borylation of aryl (pseudo)halides. Extrapolation of all three systems to a one-pot tandem borylation/Suzuki-Miyaura cross-coupling is also demonstrated on advanced intermediates and drug substances.

Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives

A full account of the total synthesis of aspidostomide B, C, their analogues and our synthetic efforts towards the synthesis of aspidostomide D, which led to the synthesis of regioisomeric N-methyl aspidostomide D, its analogues via epoxide opening strategy is presented. The synthesis of regioisomeric N-methyl aspidostomide D involves an efficient, five-step sequence, with 36.3% overall yield, starting from 3,4,5-tribromo-1H-pyrrole-2-carboxylic acid. The key features of this protocol are intramolecular cyclization, dehydration, oxidation, and a Lewis acid-mediated regioselective epoxide ring opening by C-3 position of 2,5-dibromo-1H-indole to furnish the title compounds.