3-(4-chlorobutyl)-1H-indole-5-carbonitrile

Base Information

• Chemical Name: 3-(4-chlorobutyl)-1H-indole-5-carbonitrile
• CAS No.: 143612-79-7
• Molecular Formula: C13H13 Cl N2
• Molecular Weight: 232.713
• Hs Code.: 2933990090
• European Community (EC) Number: 801-938-0
• UNII: L6DNG55PBH
• DSSTox Substance ID: DTXSID70432273
• Wikidata: Q72517647
• Mol file: 143612-79-7.mol

Synonyms:3-(4-chlorobutyl)-1H-indole-5-carbonitrile;143612-79-7;3-(4-Chlorbutyl)-1H-indol-5-carbonitril;3-(4-chlorobutyl)indole-5-carbonitrile;1H-Indole-5-carbonitrile, 3-(4-chlorobutyl)-;3-(4-chlorobutyl)-5-cyanoindole;L6DNG55PBH;UNII-L6DNG55PBH;SCHEMBL3082624;DTXSID70432273;NJJWMEJWFYRORL-UHFFFAOYSA-N;3-(4-chloro-butyl)-5-cyanoindole;BCP06422;CS-M1251;CL3519;MFCD09833261;AKOS015924756;CS-T-50582;AC-25875;AS-19269;3-(4-chlorobutyl)-1H-indol-5-carbonitrile;AM20020489;C3086;FT-0696598;A850798;A1-00284;J-510671

Chemical Property of 3-(4-chlorobutyl)-1H-indole-5-carbonitrile

Chemical Property:

• Melting Point: 99-100℃
• Boiling Point: 448.1±35.0 °C(Predicted)
• PKA: 15.93±0.30(Predicted)
• PSA: 62.30000
• Density: 1.22
• LogP: 4.26330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly, Ethyl Acetate (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 232.0767261
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

98% ^*data from raw suppliers

3-(4-Chlorobutyl)indole-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C#N)C(=CN2)CCCCCl
• Uses: Reactant in the preparation of allosteric IGF-1R inhibitors, and dual 5-HT1A receptor agonists and serotonin reuptake inhibitors.

Technology Process of 3-(4-chlorobutyl)-1H-indole-5-carbonitrile

There total 26 articles about 3-(4-chlorobutyl)-1H-indole-5-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: 95.5%

1-dimethylamino-2-(2-nitro-5-cyano)phenyl-6-chloro-n-hex-1-ene → 3-(4-chlorobutyl)-5-cyanoindole (143612-79-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 50 - 55 ℃; for 5h; under 1500.15 - 2250.23 Torr; Autoclave;

Reference yield: 92.1%

1-methoxy-2-(2-nitro-5-cyano)phenyl-6-chloro-n-hex-1-ene → 3-(4-chlorobutyl)-5-cyanoindole (143612-79-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 50 - 55 ℃; for 5h; under 1500.15 - 2250.23 Torr; Reagent/catalyst; Autoclave;

Reference yield: 89.0%

4-cyanophenyldiazonium tetrafluoroborate (2252-32-6) + 6-chlorohexylzinc bromide (135579-83-8) → 3-(4-chlorobutyl)-5-cyanoindole (143612-79-7)

Guidance literature:

With formic acid; In toluene; at -44 - 120 ℃; for 1.33333h; under 228.015 Torr; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

1H-indole-5-carbonitrile

6-chlorohexanal

6-chloro-1-hexanol

Refernces

• 1、 Heinrich, Timo,Graedler, Ulrich,Boettcher, Henning,Blaukat, Andree,Shutes, Adam. "Allosteric IGF-1R inhibitors". . p. 199 - 203. Retrieved 2010.
• 2、 Karadeolian, Avedis,Patel, Dineshkumar,Bodhuri, Prabhudas,Weeratunga, Gamini,Gorin, Boris. "Continuous Flow Process for Reductive Deoxygenation of ω-Chloroketone in the Synthesis of Vilazodone". . p. 1022 - 1028. Retrieved 2018.
• 3、 Hu, Fan,Su, Weike. "An investigation of the synthesis of vilazodone". . p. 243 - 247. Retrieved 2020/01/08.