1-Methyl-1H-indole-3-carbonyl chloride

Base Information

• Chemical Name: 1-Methyl-1H-indole-3-carbonyl chloride
• CAS No.: 126921-19-5
• Molecular Formula: C10H8 Cl N O
• Molecular Weight: 193.633
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80568739
• Nikkaji Number: J1.495.949A
• Wikidata: Q82455082
• Mol file: 126921-19-5.mol

Synonyms:1-METHYL-1H-INDOLE-3-CARBONYL CHLORIDE;126921-19-5;1-METHYLINDOLE-3-CARBONYL CHLORIDE;1H-Indole-3-carbonyl chloride, 1-methyl-;1-Methyl-1H-indole-3-carboxylic acid chloride;SCHEMBL2434450;DTXSID80568739;MCDFXFLLOVQTLA-UHFFFAOYSA-N;BFA92119;MFCD13174236;AKOS022189714;1-Methyl-1H-indole-3-carbonylchloride;1-methylindole-3-carboxylic acid chloride;N-methyl-indole-3-carboxylic acid chloride;CS-0443696;G68842

Chemical Property of 1-Methyl-1H-indole-3-carbonyl chloride

Chemical Property:

• PSA: 22.00000
• LogP: 2.55730
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 193.0294416
• Heavy Atom Count: 13
• Complexity: 219

Purity/Quality:

99%, ^*data from raw suppliers

1-Methyl-1H-indole-3-carbonylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)C(=O)Cl
• Uses: 1-Methyl-1H-indole-3-carbonyl Chloride has been used as a reactant in the preparation of indolo[2,3-a]pyrimido[5,4-c]carbazole derivatives as anti-cancer agents.

Technology Process of 1-Methyl-1H-indole-3-carbonyl chloride

There total 11 articles about 1-Methyl-1H-indole-3-carbonyl chloride 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: 100.0%

1-methyl-3-indolecarboxylic acid (32387-21-6) → 3-chlorocarbonyl-1-methylindole (126921-19-5)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

Reference yield: 99.0%

oxalyl dichloride (79-37-8) + 1-methyl-3-indolecarboxylic acid (32387-21-6) → 3-chlorocarbonyl-1-methylindole (126921-19-5)

Guidance literature:

In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → 3-chlorocarbonyl-1-methylindole (126921-19-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C / Inert atmosphere

1.2: 0 - 25 °C / Inert atmosphere

2.1: potassium permanganate / water; acetone / 5 h / 25 °C

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 25 °C / Inert atmosphere

With potassium permanganate; oxalyl dichloride; sodium hydride; N,N-dimethyl-formamide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/acs.orglett.9b00216

upstream raw materials:

1-methyl-3-indolecarboxylic acid

oxalyl dichloride

2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline

3-methoxycarbonylindole

Downstream raw materials:

4,5-bis(1-Methyl-1H-indol-3-yl)-1,2-dihydropyrazol-3-one

1-Methyl-1H-indole-3-carboxylic acid ((1R,3R,5S)-9-benzyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide

1-Methyl-1H-indole-3-carboxylic acid (2,4,6-trimethyl-phenyl)-amide

1-methyl-1H-indole-3-carboxylic acid phenylamide