4790-19-6

Basic information

• Product Name: 5,6-DIBENZYLOXYINDOLE
• Synonyms: 5,6-bis(benzyloxy)indole;5,6-bis(phenylmethoxy)-1h-indol;5,6-dibenzyloxy-indol;5,6-DIBENZYLOXYINDOLE;5,6-Bis(benzyloxy)-1H-indole;5,6-bis(phenylmethoxy)-1H-indole;NSC 83220
• CAS NO: 4790-19-6
• Molecular Formula: C₂₂H₁₉NO₂
• Molecular Weight: 329.39
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 4790-19-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 114-115℃
• Boiling Point: 525℃
• Flash Point: 185℃
• Appearance: /
• Density: 1.214
• Vapor Pressure: 1.36E-10mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: −20°C
• PKA: 16.80±0.30(Predicted)
• CAS DataBase Reference: 5,6-DIBENZYLOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIBENZYLOXYINDOLE(4790-19-6)
• EPA Substance Registry System: 5,6-DIBENZYLOXYINDOLE(4790-19-6)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• RTECS: NL6150000
• Hazardous Substances Data: 4790-19-6(Hazardous Substances Data)

Usage

Uses

Reactant for preparation of:CB2 Cannabinoid Receptor ligandsPotent c-ABL inhibitorsA potent antioxidant agent occuring naturally in beetroot

InChI:InChI=1/C22H19NO2/c1-3-7-17(8-4-1)15-24-21-13-19-11-12-23-20(19)14-22(21)25-16-18-9-5-2-6-10-18/h1-14,23H,15-16H2

Upstream product

• 4856-01-3 3,4-bis(benzyloxy)-6-nitrotoluene 
• 4966-40-9 5,6-dibenzyloxy-2-carboxy indole 
• 95704-83-9 methyl 5,6‐dibenzyloxyindole‐2‐carboxylate 
• 100-39-0 benzyl bromide 
• 1186112-99-1 4,5-dibenzyloxy-2-ethynylaniline 
• 32989-67-6 trans-4,5-dibenzyloxy-β-dimethylamino-2-nitrostyrene 
• 100-44-7 benzyl chloride 
• 1699-54-3 (E)-3,4-dibenzyloxy-β-nitrostyrene 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 98369-56-3 (E)-4,5-di(benzyloxy)-2,β-dinitrostyrene 
• 4790-17-4 ω,2-Dinitro-4,5-bis-benzyloxy-styrol 

Downstream Products

• 696612-38-1 5,6-dibenzyloxy-N-triisopropylsilylindole 
• 4821-00-5 5,6-dihydroxy-1-methylindole 
• 696612-61-0 5,5',6,6'-tetrabenzyloxy-N,N'-di(triisopropylsilyl)-3,3'-biindolyl 
• 696612-70-1 5,5',6,6'-tetrabenzyloxy-3,3'-biindolyl 
• 696612-50-7 5,6-dibenzyloxy-3-iodo-N-triisopropylsilylindole 
• 3131-52-0 1H-indole-5,6-diol 
• 129001-43-0 5,6-(Dibenzyloxy)-1-methylindole 

Relevant articles and documents

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds

(Chemical Equation Presented) A unified convenient strategy for the synthesis of 5,6-dihydroxyindole-derived 2,7′-, 2,2′-, and 2,3′-biindolyls is reported, which is based on proper manipulation of key o-ethynylaniline precursors. By the same methodology 5

Expedient synthesis of 5,6-dihydroxyindole and derivatives via an improved Zn(II)-assisted 2,β-dinitrostyrene approach

A facile 3-step synthesis of 5,6-dihydroxyindole (4a) is reported, featuring the Zn(II)-controlled regioselective nitration of 3,4- dihydroxynitrostyrene (2) with tetranitromethane at pH 8.0, and the reductive cyclization of the resulting 4,5-dihydroxy-2,β-dinitrostyrene (3a) with Na2S2O4/Zn(II) at pH 4. The latter procedure was successfully extended to the conversion of the 2,β-dinitrostyrenes 3b and 3c to 5,6-dibenzyloxyindole (4b) and 5,6-diacetoxyindole (4c) in good-to-high yields.