4790-04-9

Basic information

• Product Name: 5-Benzyloxy-6-methoxyindole
• Synonyms: 5-benzyloxy-6-methoxyindole crystalline;5-(benzyloxy)-6-methoxy-1H-indole;6-methoxy-5-(phenylmethoxy)-1H-indole;NSC 92529;5-BENZYLOXY-6-METHOXYINDOLE
• CAS NO: 4790-04-9
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.3
• Product Categories: Indole Derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles;Aromatics
• Mol File: 4790-04-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 93-94°C
• Boiling Point: 430.9°Cat760mmHg
• Flash Point: 155.3°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 3.16E-07mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 16.85±0.30(Predicted)
• CAS DataBase Reference: 5-Benzyloxy-6-methoxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Benzyloxy-6-methoxyindole(4790-04-9)
• EPA Substance Registry System: 5-Benzyloxy-6-methoxyindole(4790-04-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4790-04-9(Hazardous Substances Data)

Usage

Description

5-Benzyloxy-6-methoxyindole is an organic compound with the molecular formula C16H15NO3. It is a derivative of indole, a heterocyclic aromatic organic compound, and features a benzyloxy group at the 5-position and a methoxy group at the 6-position. 5-Benzyloxy-6-methoxyindole is known for its potential applications in various fields due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
5-Benzyloxy-6-methoxyindole is used as a reactant for the preparation of CB2 cannabinoid receptor ligands, which are important for targeting the CB2 receptors found predominantly in the immune system. These ligands have potential therapeutic applications in treating various inflammatory and immune-related disorders.
Used in Anticancer Research:
In the field of oncology, 5-Benzyloxy-6-methoxyindole is used as a potent antimitotic agent, which means it can inhibit the process of cell division, particularly in cancer cells. This property makes it a valuable compound for developing new drugs to combat cancer.
Used in Cancer Therapy:
5-Benzyloxy-6-methoxyindole is also used as a potent c-ABL inhibitor. The c-ABL protein is a non-receptor tyrosine kinase that plays a role in cell signaling and has been implicated in various cancers. Inhibiting this protein can help control the growth and spread of cancer cells.
Used in Cosmetics Industry:
In the cosmetics industry, 5-Benzyloxy-6-methoxyindole is used as a precursor for the synthesis of eu melanin pigments. These pigments are important for providing color to various cosmetic products, such as hair dyes and makeup, and can also have potential applications in skin care products for their protective and antioxidant properties.

InChI:InChI=1/C16H15NO2/c1-18-15-10-14-13(7-8-17-14)9-16(15)19-11-12-5-3-2-4-6-12/h2-10,17H,11H2,1H3

Upstream product

• 4775-68-2 ω,2-Dinitro-4-methoxy-5-benzyloxy-styrol 

Downstream Products

• 170489-21-1 5-benzyloxy-6-methoxyindole-3-carboxaldehyde 
• 1114956-72-7 N-methyl-5-benzyloxy-6-methoxy-1H-indole 
• 1048350-30-6 2-(5-(benzyloxy)-6-methoxy-1H-indol-3-yl)acetic acid 
• 1001395-59-0 N-phenylsulfonyl-5-hydroxy-6-methoxy-1H-indole 
• 1022955-71-0 2-{[6-methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine 
• 1022954-83-1 6-methoxy-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole 
• 1022953-74-7 6-methoxy-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole 
• 1022955-76-5 6-methoxy-1-methyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indole 
• 1022955-80-1 6-methoxy-1-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole 
• 1022955-73-2 N-(2-{[6-methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide 
• 1022953-72-5 4-{[(2-hydroxyethyl)(methyl)amino]methyl}-6-methoxy-1-(phenylsulfonyl)-1H-indoI-5-ol 
• 1022956-05-3 tert-butyl 6-methoxy-1-methyl-8-[(2-methylphenyl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate 
• 1022955-95-8 tert-butyl 8-[(2-chlorophenyl)sufonyl]-6-methoxy-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate 
• 1022956-14-4 tert-butyl 8-[(2,6-difluorohenyl)sufonyl]-6-methoxy-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate 

Relevant articles and documents

Silica gel assisted reductive cyclization of alkoxy-2,β-dinitrostyrenes to alkoxyindoles

-