3484-35-3

Basic information

• Product Name: 5-METHOXYINDOLE
• Synonyms: TIMTEC-BB SBB004094;RARECHEM AH BS 0117;AKOS JY2082918;5-METHOXY-1H-INDOLE;5-Methyloxindole;5-Methyl-2-oxyindole;2H-Indol-2-one, 1,3-dihydro-5-Methyl-;5-Methyl-2-oxindole
• CAS NO: 3484-35-3
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 213-745-3
• Product Categories: Indoline & Oxindole
• Mol File: 3484-35-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 52-55 °C(lit.)
• Boiling Point: 176-178 °C17 mm Hg(lit.)
• Flash Point: 109.2 °C
• Appearance: /
• Density: 1.169 g/cm³
• Storage Temp.: 2-8°C
• PKA: 14.41±0.20(Predicted)
• CAS DataBase Reference: 5-METHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYINDOLE(3484-35-3)
• EPA Substance Registry System: 5-METHOXYINDOLE(3484-35-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NL9500000
• F: 8
• Hazardous Substances Data: 3484-35-3(Hazardous Substances Data)

Usage

General Description

5-Methoxyindole is a chemical compound that belongs to the class of indole derivatives. It is most commonly known for its potential therapeutic effects, particularly in the field of medicine and pharmacology. Research has shown that 5-methoxyindole may exhibit anti-inflammatory and antioxidant properties, making it a potential candidate for the development of new drugs for the treatment of various diseases. Additionally, it has been studied for its potential role in the regulation of neurotransmitter systems and its potential anti-cancer properties. Overall, 5-methoxyindole is a versatile chemical compound with potential applications in various fields of science and medicine.

InChI:InChI=1S/C9H9NO/c1-6-2-3-8-7(4-6)5-9(11)10-8/h2-4H,5H2,1H3,(H,10,11)

Upstream product

• 37777-81-4 5-Methyl-2-nitrophenylacetic acid 
• 16634-82-5 N-(p-tolyl)-2-chloroacetamide 
• 138344-34-0 (2-tert-Butoxycarbonylamino-5-methyl-phenyl)-acetic acid 
• 614-96-0 5-methyl-1H-indole 
• 608-05-9 5-methyl-indole-2,3-dione 
• 857791-92-5 5-(5-methyl-2-oxo-indolin-3-yl)-imidazolidine-2,4-dione 
• 7732-18-5 water 
• 106-49-0 p-toluidine 
• 1581760-82-8 3,3,5’-trimethyl-3,4,5,10-tetrahydrospiro(dibenzo[b,e][1,4]diazepine-11,3’-indoline)-1,2’(2H)-dione 
• 20870-78-4 5-bromo-2-indolin-2-one 
• 80-48-8 methyl p-toluene sulfonate 
• 38939-88-7 2-chloro-4-methyl-1-nitrobenzene 
• 105-36-2 ethyl bromoacetate 
• 103-89-9 4-Methylacetanilide 

Downstream Products

• 73425-53-3 C-(6-Methyl-2,3,4,9-tetrahydro-thiopyrano[2,3-b]indol-4-yl)-methylamine 
• 24918-51-2 5-methyl-3-phenylindolin-2-one 
• 28864-72-4 5-methyl-3-phenyl-3-hydroxy-1,3-dihydro-indol-2-one 
• 1426306-63-9 C₁₆H₁₅NO 
• 923569-33-9 3-hydroxy-3-(4-methylphenyl)-5-methyl-indolin-2-one 
• 1426306-64-0 C₁₆H₁₅NO 
• 1426306-83-3 C₁₆H₁₅NO₂ 
• 1426306-65-1 C₁₆H₁₅NO 
• 1426306-66-2 C₁₇H₁₇NO 
• 1426306-67-3 3-(4-fluorophenyl)-5-methylindolin-2-one 
• 1426306-68-4 C₁₆H₁₅NO₂ 
• 728012-28-0 3-hydroxy-3-(4-methoxyphenyl)-5-methyl-1,3-dihydro-2H-indol-2-one 
• 1426306-69-5 C₁₆H₁₅NO₂ 
• 905106-99-2 3-hydroxy-3-(3-methoxyphenyl)-5-methyl-1,3-dihydro-2H-indol-2-one 

Relevant articles and documents

Following Nature’s Footprint: Mimicking the High-Valent Heme-Oxo Mediated Indole Monooxygenation Reaction Landscape of Heme Enzymes

Pathways for direct conversion of indoles to oxindoles have accumulated considerable interest in recent years due to their significance in the clear comprehension of various pathogenic processes in humans and the multipotent therapeutic value of oxindole pharmacophores. Heme enzymes are predominantly responsible for this conversion in biology and are thought to proceed with a compound-I active oxidant. These heme-enzyme-mediated indole monooxygenation pathways are rapidly emerging therapeutic targets; however, a clear mechanistic understanding is still lacking. Additionally, such knowledge holds promise in the rational design of highly specific indole monooxygenation synthetic protocols that are also cost-effective and environmentally benign. We herein report the first examples of synthetic compound-I and activated compound-II species that can effectively monooxygenate a diverse array of indoles with varied electronic and steric properties to exclusively produce the corresponding 2-oxindole products in good to excellent yields. Rigorous kinetic, thermodynamic, and mechanistic interrogations clearly illustrate an initial rate-limiting epoxidation step that takes place between the heme oxidant and indole substrate, and the resulting indole epoxide intermediate undergoes rearrangement driven by a 2,3-hydride shift on indole ring to ultimately produce 2-oxindole. The complete elucidation of the indole monooxygenation mechanism of these synthetic heme models will help reveal crucial insights into analogous biological systems, directly reinforcing drug design attempts targeting those heme enzymes. Moreover, these bioinspired model compounds are promising candidates for the future development of better synthetic protocols for the selective, efficient, and sustainable generation of 2-oxindole motifs, which are already known for a plethora of pharmacological benefits.

BENZOFURAN-BASED N-ACYLHYDRAZONE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

A benzofuran-based N-acylhydrazone derivative according to the present invention has an excellent anticancer effect while having low toxicity and excellent solubility, and, thus, a pharmaceutical composition comprising the derivative can be usefully used to prevent or treat a cell proliferative disorder including various cancers. To this end, the present invention provides a compound represented by chemical formula 1, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.

Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate

This work describes the cross-electrophile methylation of aryl bromides and aryl tosylates with methyl tosylate. The mild reaction conditions allow effective methylation of a wide set of heteroaryl electrophiles and dimethylation of dibromoarenes.