2-iodo-1H-indole

Base Information

• Chemical Name: 2-iodo-1H-indole
• CAS No.: 26340-49-8
• Molecular Formula: C8H6IN
• Molecular Weight: 243.047
• Hs Code.: 2933990090
• European Community (EC) Number: 838-780-7
• DSSTox Substance ID: DTXSID40456264
• Nikkaji Number: J464.643F
• Mol file: 26340-49-8.mol

Synonyms:2-iodo-1H-indole;26340-49-8;2-IODOINDOLE;1H-INDOLE, 2-IODO-;iodoindole;SCHEMBL2551202;DTXSID40456264;ZPIHHIRJUPXETJ-UHFFFAOYSA-N;AMY32380;BBA34049;MFCD10699391;AKOS016008811;DS-4612;MB08792;EN300-227443;F18254;A877252

Chemical Property of 2-iodo-1H-indole

Chemical Property:

• Melting Point: 79-81 °C
• Boiling Point: 341.7±15.0 °C(Predicted)
• PKA: 15.57±0.30(Predicted)
• PSA: 15.79000
• Density: 1.960±0.06 g/cm3(Predicted)
• LogP: 2.77250
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 242.95450
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

97% ^*data from raw suppliers

2-Iodoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)I
• Uses: 2-Iodoindole is used in the synthesis of arylthioindole molecules as a class of tubulin polymerization inhibitors. Also used in the synthesis of combretastatin A-4 derivatives.

Technology Process of 2-iodo-1H-indole

There total 11 articles about 2-iodo-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: 91.0%

indole (120-72-9) → 2-iodo-1H-indole (26340-49-8)

Guidance literature:

With n-butyllithium; 1,2-Diiodoethane; carbon dioxide; tert.-butyl lithium; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)10088-0

Reference yield: 89.0%

2-iodo-1-(phenylsulfonyl)-1H-indole (99275-44-2) → 2-iodo-1H-indole (26340-49-8)

Guidance literature:

With potassium carbonate; In ethanol; for 2.5h; Heating;

DOI:10.1002/jhet.5570220260

Reference yield: 55.0%

1-benzenesulfonylindole (40899-71-6) → 2-iodo-1H-indole (26340-49-8)

Guidance literature:

1-benzenesulfonylindole; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 2.5h;

With iodine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 20h;

With sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 3h;

DOI:10.1055/s-0036-1588461

upstream raw materials:

indole

2-iodo-1-<<2-(trimethylsilyl)ethoxy>methyl>indole

2-iodo-1-(phenylsulfonyl)-1H-indole

indole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

2-iodo-1-methyl-1H-indole

1-benzenesulfonyl-1H,1'H-[2,2']biindolyl

1-benzyl-2-(indol-2'-yl)indole

1-benzyl-2-iodo-1H-indole

Refernces

Convenient synthesis of bis(3-indolyl)-acetylene via Sonogashira coupling

10.1080/00397910601133631

The study presents a convenient synthesis method for bis(3-indolyl)acetylene, a potentially important class of molecules for heterocycle synthesis. The process involves a Pd-catalyzed cross-coupling reaction of iodoindole and 3-indolylacetylene, followed by deprotection to yield the final product. Key chemicals used include iodoindole, 3-indolylacetylene, Pd(PPh3)4 as a catalyst, and CuI as a co-catalyst. These chemicals serve to facilitate the coupling reaction and protect the intermediate products, ultimately leading to the synthesis of phenylsulfonyl-protected and unprotected bis(3-indolyl)acetylenes. The study also discusses the ongoing chemistry of these internal alkynes in the laboratory, indicating further research in this area.