4-Isoquinolin-3-YL-butyronitrile

Base Information

• Chemical Name: 4-Isoquinolin-3-YL-butyronitrile
• CAS No.: 396717-24-1
• Molecular Formula: C₁₃H₁₂N₂
• Molecular Weight: 196.252
• DSSTox Substance ID: DTXSID20447650
• Nikkaji Number: J1.695.143I
• ChEMBL ID: CHEMBL1368512
• Mol file: 396717-24-1.mol

Synonyms:396717-24-1;4-(isoquinolin-3-yl)butanenitrile;4-ISOQUINOLIN-3-YL-BUTYRONITRILE;3-Isoquinolinebutanenitrile;Isoquinoline 3-butanenitrile;MLS001361024;ISUPSL100481;4-Isoquinolin-3-ylbutyronitrile;CHEMBL1368512;DTXSID20447650;HMS3098B16;AKOS006287186;SMR001216505;FT-0695627;N-Ethyl-N-(2-hydroxy-3-sulfopropyl)-3,5-dimethoxyanilinesodiumsalt

Chemical Property of 4-Isoquinolin-3-YL-butyronitrile

Chemical Property:

• PSA: 36.68000
• LogP: 3.08108
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 196.100048391
• Heavy Atom Count: 15
• Complexity: 240

Purity/Quality:

98.5% ^*data from raw suppliers

4-ISOQUINOLIN-3-YL-BUTYRONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=NC(=CC2=C1)CCCC#N

Technology Process of 4-Isoquinolin-3-YL-butyronitrile

There total 7 articles about 4-Isoquinolin-3-YL-butyronitrile 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: 87.0%

6-[2-(tert-butylimino-methyl)-phenyl]-hex-5-ynenitrile (475292-86-5) → 4-(isoquinolin-3-yl)butanenitrile (396717-24-1)

Guidance literature:

copper(l) iodide; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

DOI:10.1021/jo010579z

Reference yield: 84.0%

5-hexynonitrile (14918-21-9) + (E)-N-(2-iodobenzylidene)-2-methylpropan-2-amine → 4-(isoquinolin-3-yl)butanenitrile (396717-24-1)

Guidance literature:

With zinc; dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II); In acetonitrile; at 80 ℃; for 0.333333h;

DOI:10.1021/ol0519994

Reference yield:

5-hexynonitrile (14918-21-9) → 4-(isoquinolin-3-yl)butanenitrile (396717-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CuI; Et₃N / PdCl₂(PPh₃)2 / 1 h / 55 °C

2: 87 percent / CuI / dimethylformamide / 3 h / 100 °C

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide;

DOI:10.1021/jo010579z

upstream raw materials:

6-[2-(tert-butylimino-methyl)-phenyl]-hex-5-ynenitrile

5-hexynonitrile

2-iodobenzaldehyde

N-(2-iodobenzylidene)-2-methylpropan-2-amine

Refernces

• 1、 Korivi, Rajendra Prasad,Cheng, Chien-Hong. "Highly efficient synthesis of isoquinolines via nickel-catalyzed annulation of 2-iodobenzaldimines with alkynes: Evidence for dual pathways of alkyne insertion". . p. 5179 - 5182. Retrieved 2007/10/03.