3-iodo-1H-indole-2-carbonitrile

Base Information

• Chemical Name: 3-iodo-1H-indole-2-carbonitrile
• CAS No.: 51796-65-7
• Molecular Formula: C9H5IN2
• Molecular Weight: 268.057
• Hs Code.: 2933998090
• European Community (EC) Number: 695-386-6
• DSSTox Substance ID: DTXSID60453139
• Wikidata: Q82274173
• Mol file: 51796-65-7.mol

Synonyms:3-iodo-1H-indole-2-carbonitrile;51796-65-7;SCHEMBL16156592;DTXSID60453139;BCA79665;MFCD22126121;AKOS015991306;CG-0745;CS-0453223

Chemical Property of 3-iodo-1H-indole-2-carbonitrile

Chemical Property:

• Boiling Point: 431.1±30.0 °C(Predicted)
• PKA: 12.41±0.30(Predicted)
• PSA: 39.58000
• Density: 2.00±0.1 g/cm3(Predicted)
• LogP: 2.64418
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 267.94975
• Heavy Atom Count: 12
• Complexity: 220

Purity/Quality:

98%min ^*data from raw suppliers

3-Iodo-1H-indole-2-carbonitrile 97% ^*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)C#N)I

Technology Process of 3-iodo-1H-indole-2-carbonitrile

There total 11 articles about 3-iodo-1H-indole-2-carbonitrile 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: 77.0%

1H-indole-2-carbonitrile (36193-65-4) → 3-iodo-1H-indole-2-carbonitrile (51796-65-7)

Guidance literature:

1H-indole-2-carbonitrile; With potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

With iodine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h;

DOI:10.3390/molecules26175287

Reference yield: 22.0%

1H-indole-2-carbonitrile (36193-65-4) → 3-iodo-1H-indole-2-carbonitrile (51796-65-7) + 2,2'-Dicyano-3,3'-bis (51796-62-4)

Guidance literature:

With iodine; In xylene; 1.) 140 deg C, 6 h, 2.) cooling, 10 h;

DOI:10.1021/jo01314a020

Reference yield:

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → 3-iodo-1H-indole-2-carbonitrile (51796-65-7)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / diethyl ether / 0.67 h / 20 °C

2: NH₃ / diethyl ether / 24 h / 20 °C

3: POCl₃ / 0.08 h / Heating

4: 0.56 g / KOH; I₂ / dimethylformamide / 4 h / 20 °C

With potassium hydroxide; thionyl chloride; ammonia; iodine; trichlorophosphate; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo026178g

upstream raw materials:

1H-indole-2-carbonitrile

1H-indol-2-ylcarboxaldehyde

2-(hydroxymethyl)indole

1H-indole-2-carboxamide

Refernces

• 1、 Praveen, Chandrasekaran,Dheenkumar,Perumal. "Super acid catalysed sequential hydrolysis/cycloisomerization of o-(acetylenic)benzamides under microwave condition: Synthesis, antinociceptive and antiinflammatory activity of substituted isocoumarins". . p. 71 - 83. Retrieved 2013/05/09.
• 2、 Abramovitch, Rudolph A.,Cue, Berkeley W.. "Ring Contraction of 2-Azidoquinoline and Quinoxaline 1-Oxides". . p. 5316 - 5319. Retrieved 2007/10/02.