methyl 3-iodo-1H-indole-6-carboxylate

Base Information

• Chemical Name: methyl 3-iodo-1H-indole-6-carboxylate
• CAS No.: 850374-98-0
• Molecular Formula: C10H8 I N O2
• Molecular Weight: 301.084
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID30427822
• Wikidata: Q82240533
• Mol file: 850374-98-0.mol

Synonyms:methyl 3-iodo-1H-indole-6-carboxylate;850374-98-0;SCHEMBL19475912;DTXSID30427822;TQP1288;MFCD06797504;SB15315;MS-22267;CS-0069918;FT-0742811;D73858

Chemical Property of methyl 3-iodo-1H-indole-6-carboxylate

Chemical Property:

• Vapor Pressure: 7.22E-07mmHg at 25°C
• Melting Point: 150(dec.)
• Refractive Index: 1.709
• Boiling Point: 408°C at 760 mmHg
• Flash Point: 200.6°C
• PSA: 42.09000
• Density: 1.86g/cm³
• LogP: 2.55910
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 300.95998
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 3-iodo-1H-indole-6-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)C(=CN2)I

Technology Process of methyl 3-iodo-1H-indole-6-carboxylate

There total 2 articles about methyl 3-iodo-1H-indole-6-carboxylate 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: 95.0%

indole-6-carboxylic acid methyl ester (50820-65-0) → 3-iodo-1H-indole-6-carboxylic acid methyl ester (850374-98-0)

Guidance literature:

With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/chem.201602416

Reference yield:

Indole-6-carboxylic acid (1670-82-2,261352-47-0) → 3-iodo-1H-indole-6-carboxylic acid methyl ester (850374-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / Inert atmosphere

1.2: 2 h

2.1: iodine; potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C

With iodine; potassium carbonate; potassium hydroxide; In N,N-dimethyl-formamide;

Reference yield: 91.0%

3-iodo-1H-indole-6-carboxylic acid methyl ester (850374-98-0) + p-toluenesulfonyl chloride (98-59-9) → methyl 3-iodo-1-tosyl-1H-indole-6-carboxylate (1432521-55-5)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tet.2013.01.001

upstream raw materials:

indole-6-carboxylic acid methyl ester

Indole-6-carboxylic acid

Downstream raw materials:

1-t-butoxycarbonyl-3-iodo-1H-indole-6-carboxylic acid methyl ester

methyl 3-(2-(2,2-dibromovinyl)phenyl)-1-tosyl-1H-indole-6-carboxylate

methyl 3-(2-formylphenyl)-1-tosyl-1H-indole-6-carboxylate

methyl 3-iodo-1-tosyl-1H-indole-6-carboxylate

Refernces

• 1、 -. "RORγ MODULATORS". Page/Page column 32-33. . Retrieved 2018/04/13.
• 2、 Livendahl, Madeleine,Jamroskovic, Jan,Ivanova, Svetlana,Demirel, Peter,Sabouri, Nasim,Chorell, Erik. "Design and Synthesis of 2,2′-Diindolylmethanes to Selectively Target Certain G-Quadruplex DNA Structures". supporting information. p. 13004 - 13009. Retrieved 2016/09/09.