15903-94-3

Basic information

• Product Name: 6-Benzyloxyindole
• Synonyms: 6-BENZYLOXYINDOLE;6-(Benzyloxy)-1H-indole; NSC 92538;6-(Phenylmethoxy)-1H-indole;6-(Benzyloxy)-1H-indole 98%;6-BENZYLOXYINDOLE 97%;6-Benzyloxyindole ,98%;NH6-Benzyloxyindole
• CAS NO: 15903-94-3
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.27
• EINECS: -0
• Product Categories: blocks;IndolesOxindoles;Indoline & Oxindole;Heterocyclic Compounds;Indole Series;Aromatics Compounds;Indoles;Simple Indoles;Indole;Aromatics;Indole Derivatives;Building Blocks;Heterocyclic Building Blocks;Heterocycle-Indole series
• Mol File: 15903-94-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 116-119°C
• Boiling Point: 411.6 °C at 760 mmHg
• Flash Point: 148.9 °C
• Appearance: yellow to brown/crystalline
• Density: 1.196 g/cm³
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Diethyl Ether (Slightly), Ethanol (Slightly), Ethyl Aceta
• PKA: 17.17±0.30(Predicted)
• BRN: 173319
• CAS DataBase Reference: 6-Benzyloxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Benzyloxyindole(15903-94-3)
• EPA Substance Registry System: 6-Benzyloxyindole(15903-94-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 15903-94-3(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Crystalline Solid

Uses

Different sources of media describe the Uses of 15903-94-3 differently. You can refer to the following data:
1. Indole derivative, as antiviral and antitumor agent
2. Reactant for enantioselective synthesis of quaternary carbon-containing 3-(3-indolyl)isoindolin-1-onesReactant for Friedel-Crafts alkylation reactions with hydroxyisoindolinonesReactant for direct and regioselective synthesis of β-heteroarylated ketonesReactant for preparation of hepatitis C virus (HCV) inhibitorsReactant for preparation of protein kinase C (PKC) inhibitorsReactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands

InChI:InChI=1/C15H13NO/c1-2-4-12(5-3-1)11-17-14-7-6-13-8-9-16-15(13)10-14/h1-10,16H,11H2

Upstream product

• 1484-26-0 3-(benzyloxy)aniline 
• 40047-21-0 (4-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 2380-86-1 6-hydroxy-1H-indole 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 24239-67-6 4-(benzyloxy)-1-methyl-2-nitrobenzene 
• 2042-14-0 4-methyl-5-nitrophenol 
• 40047-20-9 6-benzyloxy-indole-2-carboxylic acid ethyl ester 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 153805-86-8 3-Benzyloxy-6-(2-pyrrolidinylvinyl)nitrobenzene 
• 99474-13-2 (E)-5-(benzyloxy)-2-<2-(dimethylamino)vinyl>nitrobenzene 
• 109532-26-5 2-Amino-4-(benzyloxy)-α-chloracetophenon 
• 40047-22-1 6-(benzyloxy)-1H-indole-2-carboxylic acid 

Downstream Products

• 158863-21-9 6-Benzyloxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole 
• 116725-92-9 1-(6-benzyloxy-1H-indol-3-yl)-2-chloroethanone 
• 158147-87-6 (4R,5R)-1-<2-(6-benzyloxy-1H-indol-3-yl)-2-oxoethyl>-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester 
• 848086-48-6 3-[4-(6-Benzyloxy-1H-indol-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester 
• 174402-47-2 3-(6-Benzyloxy-1H-indol-3-yl)-4-[6-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-1-methyl-pyrrole-2,5-dione 
• 220873-36-9 3-(6-benzyloxy-1H-indol-3-yl)-1-benzyloxymethyl-4-bromo-pyrrole-2,5-dione 
• 220873-42-7 3-(6-Benzyloxy-1H-indol-3-yl)-1-benzyloxymethyl-4-[6-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 188884-38-0 3-(6-Benzyloxy-1H-indol-3-yl)-1-methyl-4-[1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 848086-47-5 3-(6-Benzyloxy-1H-indol-3-yl)-4-[5-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-1-methyl-pyrrole-2,5-dione 
• 294862-88-7 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole 
• 1476-33-1 2-(6-(hydroxy)-1H-indol-3-yl)-N,N-dimethylethanamine 
• 31677-74-4 2-(6-benzyloxy-indol-3-yl)-ethylamine 

Relevant articles and documents

Total Synthesis of Bruceolline i

The first total synthesis of the natural product bruceolline I, isolated in small quantities from the ethanol extract of Brucea mollis stems, was achieved in 29% yield over nine steps and with high enantiomeric purity (>98%). The key step of the process i

Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity

The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1-n-octyl-1H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-fused ring motif was affirmed by SAR and validated in a mouse model of tuberculosis. As expected for membrane inserting agents, the indolyl azaspiroketal Mannich bases perturbed phospholipid vesicles, permeabilized bacterial cells, and induced the mycobacterial cell envelope stress reporter promoter piniBAC. Surprisingly, their membrane disruptive effects did not appear to be associated with bacterial membrane depolarization. This profile was not uniquely associated with azaspiroketal Mannich bases but was characteristic of indolyl Mannich bases as a class. Whereas resistant mycobacteria could not be isolated for a less potent indolyl Mannich base, the more potent azaspiroketal analog displayed low spontaneous resistance mutation frequency of 10-8/CFU. This may indicate involvement of an additional envelope-related target in its mechanism of action.

Structure-based de novo design, synthesis, and biological evaluation of the indole-based PPARγ ligands (I)

MCSS and LeapFrog, two de novo drug design programs, were used for the novel indole-based PPARγ ligands' study. The designed compounds were synthesized and tested for the PPARγ protein binding activities in vitro. Out of the compounds that were synthesize