16382-21-1

Basic information

• Product Name: 1-benzyl-5-methoxy-1H-indole
• CAS NO: 16382-21-1
• Molecular Formula: C₁₆H₁₅NO
• Molecular Weight: 237.2964
• Mol File: 16382-21-1.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 412.4°C at 760 mmHg
• Flash Point: 203.2°C
• Density: 1.07g/cm³
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 1-benzyl-5-methoxy-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-methoxy-1H-indole(16382-21-1)
• EPA Substance Registry System: 1-benzyl-5-methoxy-1H-indole(16382-21-1)

Safety Data

• Hazardous Substances Data: 16382-21-1(Hazardous Substances Data)

Usage

Chemical class

Indole alkaloids
A group of naturally occurring nitrogen-containing compounds with diverse biological activities.
2. Derivative of 5-methoxy-1H-indole
Modified version of the naturally occurring compound, 5-methoxy-1H-indole, with additional functional groups.
3. Benzyl group attachment
A benzyl group (C6H5CH2-) is attached to the indole ring, which influences the compound's properties and pharmacological effects.
4. Potential pharmacological properties
The compound has been studied for its possible effects on the body, including its role as a psychoactive and hallucinogenic drug.
5. Medicinal chemistry applications
Researchers are exploring the potential use of 1-benzyl-5-methoxy-1H-indole in the development of new pharmaceuticals.
6. Relevance to multiple research fields
The compound's structure and properties make it of interest to researchers in organic chemistry, pharmacology, and drug discovery.

Upstream product

• 1006-94-6 5-methoxylindole 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 21857-45-4 5-methoxyindoline 
• 100-51-6 benzyl alcohol 
• 67-56-1 methanol 
• 92433-38-0 1-benzyl-5-chloro-1H-indole 
• 10365-98-7 3-methoxyphenylboronic acid 
• 10075-51-1 1-benzyl-5-bromo-1H-indole 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 74492-44-7 1-benzyl-5-methoxyindoline 
• 625842-54-8 N-(2,2-diethoxyethyl)-4-methoxyaniline 
• 1429616-63-6 N-benzyl-N-(2,2-diethoxyethyl)-4-methoxyaniline 
• 10075-50-0 5-bromo-1H-indole 

Downstream Products

• 142769-36-6 1-benzyl-1H-indol-5-ol 
• 348637-35-4 1-benzyl-5-methoxy-1H-indole-3-carbonitrile 
• 1567403-53-5 (S)-3-(1-benzyl-5-methoxy-1H-indol-3-yl)-1-(1-methyl-1H-imidazol-2-yl)butan-1-one 
• 1529806-71-0 N-((1-benzyl-5-methoxy-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide 
• 1529806-90-3 9-benzyl-6-methoxy-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydrospiro[pyrido[3,4-b]indole-4,2'-pyrrole] 
• 1584220-68-7 C₂₄H₂₄N₂O₃S 
• 1584220-56-3 C₂₄H₂₂N₂O₃S 
• 178047-39-7 5-methoxy-2-indolecarboxaldehyde 
• 94310-54-0 N-benzyl-3-isopropyl-5-methoxyindole 
• 1423160-23-9 3-ethoxycarbonyl-3-(1-benzyl-5-methoxyindol-3-yl)isoindolin-1-one 
• 1416166-35-2 1-benzyl-5-methoxy-2-((triisopropylsilyl)ethynyl)-1H-indole 

Relevant articles and documents

Design, synthesis, evaluation, and molecular modeling studies of indolyl oxoacetamides as potential pancreatic lipase inhibitors

A series of indolyl oxoacetamide analogs was synthesized, characterized, and evaluated for their pancreatic lipase inhibitory activity using porcine pancreatic lipase (type II) and 4-nitrophenyl butyrate. Compound 8d exhibited a potent inhibition, with an IC50 value of 4.53 μM, followed by 8c (IC50 = 5.12 μM), compared with the standard drug, orlistat (IC50 = 0.99 μM). Furthermore, analogs 8c and 8d exhibited a reversible competitive inhibition, similar to orlistat. Molecular docking studies of the compounds 7a–f and 8a–f were in agreement with the in vitro results, wherein 8d exhibited a potential MolDock score of ?163.052 kcal/mol. A 10-ns molecular dynamics simulation of 8d complexed with pancreatic lipase confirmed the role of π–π stacking and π–cation interactions with the lid domain and Arg 256, respectively, in stabilizing the ligand at the active site (maximum observed root mean square deviation ≈ 2 ?). The present study led to the identification of novel indolyl oxoacetamides (8a–d) as potential pancreatic lipase inhibitory leads that might further result in enhanced potency through lead optimization.

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Three-component reactions of 3-arylidene-3h-indolium salts, isocyanides and amines

A multicomponent reaction of isocyanides with aryl(indol-3-yl)methylium salts and amines has been found. A series of aryl(indol-3-yl)acetimidamides was obtained in up to 96% yields. In the case of ethyl isocyanoacetate, the reaction is followed by cyclization to form 3,5-dihydro-4H-imidazol-4-one derivatives.