3420-02-8

Basic information

• Product Name: 6-Methylindole
• Synonyms: Indole, 6-methyl-;6-METHYL-1H-INDOLE;6-METHYLINDOLE;AKOS JY2082811;6-Methyindole;6-Methylindole,98%;6-Metlylindole;1H-Indole,6-methyl-
• CAS NO: 3420-02-8
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• Product Categories: blocks;IndolesOxindoles;Indoles and derivatives;Pyrroles & Indoles;Indoles;Simple Indoles;Indole;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Heterocycles
• Mol File: 3420-02-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 29-32°C
• Boiling Point: 112 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to light brown/Liquid After Melting
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: n20/D 1.607(lit.)
• Storage Temp.: 0-6°C
• PKA: 17.36±0.30(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 109708
• CAS DataBase Reference: 6-Methylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methylindole(3420-02-8)
• EPA Substance Registry System: 6-Methylindole(3420-02-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• HazardClass: IRRITANT, LIGHT SENSITIVE
• Hazardous Substances Data: 3420-02-8(Hazardous Substances Data)

Usage

Description

6-Methylindole, also known as 1H-indole-6-methanol, is an organic compound with a molecular formula of C9H9N. It is a heterocyclic aromatic compound derived from indole, featuring a methyl group attached to the 6th position of the indole ring. 6-Methylindole is known for its versatile chemical properties and is widely utilized in the synthesis of various pharmaceutical compounds and biologically active molecules.

Uses

Used in Pharmaceutical Synthesis:
6-Methylindole is used as a key reactant in the synthesis of various pharmaceutical compounds, including:
1. Benz[c,d]indol-3(1H)-one derivatives: These compounds have potential applications in the development of novel therapeutic agents.
2. Tryptophan dioxygenase inhibitors, such as pyridyl-ethenyl-indoles: These are potential anticancer immunomodulators, which can modulate the immune system to combat cancer cells.
3. Indole linked triazole derivatives: These compounds exhibit antifungal properties and can be used in the development of antifungal agents.
4. N-β-D-xylosyl-indole derivatives: These are SGLT2 inhibitors, which can be used for the management of hyperglycemia in diabetes patients.
5. Aminoguanidine derivatives of arylsulfonylacylindoles: These compounds have potential applications as antifungal agents.
6. Indolylindazoles and indolylpyrazolopyridines: These compounds act as interleukin-2 inducible T cell kinase inhibitors, which can be used in the development of immunomodulatory drugs.
7. Arylsulfonylacetylindoles: These compounds have potential applications as anti-HIV-1 agents, targeting the human immunodeficiency virus.

InChI:InChI=1/C9H9N/c1-7-2-3-8-4-5-10-9(8)6-7/h2-6,10H,1H3

Upstream product

• 54664-51-6 4-methyl-β-phenethylsulfonyl azide 
• 75934-37-1 N-(2,2-Diethoxy-ethyl)-2,2,2-trifluoro-N-m-tolyl-acetamide 
• 102-71-6 triethanolamine 
• 108-44-1 1-amino-3-methylbenzene 
• 637-39-8 triethanolamine hydrochloride 
• 107-21-1 ethylene glycol 

Downstream Products

• 35998-04-0 N,N-dimethyl-1-(6-methyl-1H-indol-3-yl)methanamine 
• 4771-49-7 6-methyl-1H-indole-3-carboxaldehyde 
• 676476-82-7 2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)-ethanone 
• 408356-30-9 methyl 2-(6-methyl-1H-indol-3-yl)oxoacetate 
• 957373-16-9 C₁₉H₂₁NO 
• 1095885-61-2 4-[6-(methyl)-1H-indol-1-yl]benzamide 
• 1194041-99-0 N-(3-nitrobenzene)sulfonyl-6-methylindole 
• 1228311-91-8 1-(6-methyl-1H-indol-3-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1246025-26-2 (R)-4,4,4-trifluoro-3-(6-methyl-1H-indol-3-yl)-1-phenylbutan-1-one 
• 1258065-96-1 (E)-2-benzylidene-4-(6-methyl-1H-indol-3-yl)cyclopentanone 

Relevant articles and documents

β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction

Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.

Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles

Anilines react with alkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180°C in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2·2H2O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2·2H2O is necessary for the effective formation of indoles. A reaction pathway involving alkanol group transfer from alkanolamines to anilines, N-alkylation of anilines by anilinoalkanols and heteroannulation of 1,2-dianilinoalkanes is proposed for this catalytic process.

Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin(II) chloride dihydrate

Anilines react with trialkanolamines in dioxane in the presence of a catalytic amount of a ruthenium catalyst together with tin(II) chloride dihydrate to give the corresponding indoles in moderate to good yields.