2-(5-chloro-1H-indol-3-yl)acetonitrile

Base Information

• Chemical Name: 2-(5-chloro-1H-indol-3-yl)acetonitrile
• CAS No.: 81630-83-3
• Molecular Formula: C10H7ClN2
• Molecular Weight: 190.632
• Hs Code.: 2933990090
• European Community (EC) Number: 872-153-9
• DSSTox Substance ID: DTXSID60489130
• Wikidata: Q72452246
• Mol file: 81630-83-3.mol

Synonyms:2-(5-chloro-1H-indol-3-yl)acetonitrile;81630-83-3;5-Chloro-3-cyanomethyl-1H-indole;(5-chloro-1H-indol-3-yl)-acetonitrile;2-(5-chloranyl-1H-indol-3-yl)ethanenitrile;SCHEMBL446591;5-chloro-indole-3-acetonitrile;DTXSID60489130;UHFZUNGNGGEESB-UHFFFAOYSA-N;MFCD09751323;AKOS013192188;(5-Chloro-1H-indol-3-yl)acetonitrile;CS-0142302;FT-0691092;EN300-82448;A840175;Z1162450204;LVF

Chemical Property of 2-(5-chloro-1H-indol-3-yl)acetonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• Boiling Point: 406.517 °C at 760 mmHg
• Flash Point: 199.655 °C
• PSA: 39.58000
• Density: 1.361 g/cm³
• LogP: 2.88738
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 190.0297759
• Heavy Atom Count: 13
• Complexity: 232

Purity/Quality:

98%Min ^*data from raw suppliers

5-Chloro-3-cyanomethyl-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)C(=CN2)CC#N

Technology Process of 2-(5-chloro-1H-indol-3-yl)acetonitrile

There total 8 articles about 2-(5-chloro-1H-indol-3-yl)acetonitrile 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: 68.0%

potassium cyanide + 5-chloro-1H-indole-3-carboxaldehyde (827-01-0) → 2-(5-chloro-1H-indol-3-yl)acetonitrile (81630-83-3)

Guidance literature:

5-chloro-1H-indole-3-carboxaldehyde; With sodium tetrahydroborate; In methanol; formamide; at 20 ℃; for 0.25h;

potassium cyanide; In methanol; formamide; at 55 ℃; for 16h;

DOI:10.1016/j.ejmech.2018.07.011

Reference yield: 63.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + trimethylsilyl cyanide (7677-24-9) + 5-chloro-1H-indole (17422-32-1) → 2-(5-chloro-1H-indol-3-yl)acetonitrile (81630-83-3)

Guidance literature:

formaldehyd; 5-chloro-1H-indole; With acetic acid; dimethyl amine; In water; at 20 ℃; for 6h;

With 3-(Dimethylaminomethyl)indole; methyl iodide; In dichloromethane; toluene; at 20 ℃; for 12h;

trimethylsilyl cyanide; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

Reference yield: 63.0%

3-(Dimethylaminomethyl)indole (87-52-5) + 5-chloro-1H-indole (17422-32-1) + methyl iodide (74-88-4) → 2-(5-chloro-1H-indol-3-yl)acetonitrile (81630-83-3)

Guidance literature:

With sodium hydroxide; formaldehyd; tetrabutyl ammonium fluoride; acetic acid; dimethyl amine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;

upstream raw materials:

3-(dimethylaminomethyl)-5-chloro-1H-indole

5-chloro-1H-indole

3-(Dimethylaminomethyl)indole

methyl iodide

Downstream raw materials:

5-chlorotryptamine

2-(5-chloro-1H-indol-3-yl)acetic acid

Refernces

• 1、 Egami, Hiromichi,Hotta, Ryo,Otsubo, Minami,Rouno, Taiki,Niwa, Tomoki,Yamashita, Kenji,Hamashima, Yoshitaka. "Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst". supporting information. p. 5656 - 5660. Retrieved 2020/07/14.
• 2、 -. "SELECTIVE ANTI-CANCER COMPOUNDS". Page/Page column 82-83. . Retrieved 2017/01/31.