4,6-Dimethoxy-3-methyl-1H-indole

Base Information

• Chemical Name: 4,6-Dimethoxy-3-methyl-1H-indole
• CAS No.: 74973-30-1
• Molecular Formula: C11H13 N O2
• Molecular Weight: 191.23
• Hs Code.: 2933990090
• European Community (EC) Number: 623-128-4
• DSSTox Substance ID: DTXSID00505267
• Nikkaji Number: J2.682.487G
• Wikidata: Q82360256
• Mol file: 74973-30-1.mol

Synonyms:4,6-Dimethoxy-3-methyl-1H-indole;74973-30-1;4,6-Dimethoxy-3-methylindole;4,6-DIMETHOXY-3-METHYLINDOLE,97%;4,6-DIMETHOXY-3-METHYLINDOLE, 97%;SCHEMBL24825685;DTXSID00505267

Chemical Property of 4,6-Dimethoxy-3-methyl-1H-indole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 83-86 °C
• Refractive Index: 1.598
• Boiling Point: 353.49°C at 760 mmHg
• Flash Point: 129.098°C
• PSA: 34.25000
• Density: 1.151g/cm³
• LogP: 2.49350
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 198

Purity/Quality:

98%Min ^*data from raw suppliers

4,6-Dimethoxy-3-methylindole 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CNC2=C1C(=CC(=C2)OC)OC
• Uses: Reactant for:? ;Acid-catalyzed reactions with ketones1? ;Synthesis of pyrrolo[1,2-a]indoles2? ;Synthesis of indolo[2,3-c]quinolines3? ;Nitration and oxidative dimerization reactions with nitric acid4 Reactant for:Acid-catalyzed reactions with ketonesSynthesis of pyrrolo[1,2-a]indolesSynthesis of indolo[2,3-c]quinolinesNitration and oxidative dimerization reactions with nitric acid

Technology Process of 4,6-Dimethoxy-3-methyl-1H-indole

There total 7 articles about 4,6-Dimethoxy-3-methyl-1H-indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-(4,6-dimethoxy-3-methyl-1H-indol-1-yl)ethan-1-one (827024-88-4) → 3-methyl-4,6-dimethoxyindole (74973-30-1)

Guidance literature:

With potassium hydroxide; In ethanol; for 2h;

DOI:10.1016/j.tet.2004.10.060

Reference yield: 74.0%

chloroacetone (78-95-5) + 3.5-dimethoxyaniline (10272-07-8) → 3-methyl-4,6-dimethoxyindole (74973-30-1)

Guidance literature:

With sodium hydrogencarbonate; lithium bromide; In ethanol; for 6h; Heating;

DOI:10.1016/j.tet.2004.10.060

Reference yield: 58.0%

ethyl 3-hydroxy-4,6-dimethoxylindolin-2-one-3-carboxylate (23659-85-0) → 3-methyl-4,6-dimethoxyindole (74973-30-1)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In 1,4-dioxane; at 60 ℃; for 3.5h;

DOI:10.1016/0040-4020(96)00441-3

upstream raw materials:

ethyl 3-hydroxy-4,6-dimethoxylindolin-2-one-3-carboxylate

chloroacetone

3.5-dimethoxyaniline

1-(4,6-dimethoxy-3-methyl-1H-indol-1-yl)ethan-1-one

Downstream raw materials:

3-(4,6-Dimethoxy-3-methyl-1H-indol-2-yl)-1,3-bis-(4-ethyl-phenyl)-6,8-dimethoxy-1,9-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole

3-(4,6-Dimethoxy-3-methyl-1H-indol-2-yl)-6,8-dimethoxy-1,9-dimethyl-1,3-di-p-tolyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole

4,27-dimethyl-2-(4-nitrophenyl)-6,8,23,25-tetramethoxy-11,20-diazahexacyclo[18,7,0,0(3,11),0(5,10),0(13,18),0(21,26)]heptacosa-1⁽²⁷⁾,3,5,7,9,13,15,17,21,23,25-undecaene

2-(4-chlorophenyl)-4,27-dimethyl-6,8,23,25-tetramethoxy-11,20-diazahexacyclo[18,7,0,0(3,11),0(5,10),0(13,18),0(21,26)]heptacosa-1⁽²⁷⁾,3,5,7,9,13,15,17,21,23,25-undecaene

Refernces

• 1、 Black, David St.C.,Kumar, Naresh,McConnell, Darryl B.. "Reaction of some 4,6-dimethoxyindoles with oxalyl chloride". . p. 8925 - 8936. Retrieved 2007/10/03.
• 2、 Black, David St. C.,Rothnie, Neil E.,Wong, Laurence C. H.. "SYNTHESIS OF MACROCYCLIC LIGANDS CONTAINING THE INDOLE RING SYSTEM". . p. 1883 - 1886. Retrieved 2007/10/02.