2-Ethynylisonicotinonitrile

Base Information

• Chemical Name: 2-Ethynylisonicotinonitrile
• CAS No.: 1211580-87-8
• Molecular Formula: C₈H₄N₂
• Molecular Weight: 128.133
• DSSTox Substance ID: DTXSID701302618
• Mol file: 1211580-87-8.mol

Synonyms:2-ETHYNYLISONICOTINONITRILE;1211580-87-8;2-ethynylpyridine-4-carbonitrile;2-Ethynyl-isonicotinonitrile;SCHEMBL2717380;2-Ethynyl-4-pyridinecarbonitrile;DTXSID701302618;MFCD18205182;AKOS022178696;EN300-7551382;F2167-2837

Chemical Property of 2-Ethynylisonicotinonitrile

Chemical Property:

• Boiling Point: 236.1±25.0 °C(Predicted)
• PKA: -1.09±0.20(Predicted)
• Density: 1.15±0.1 g/cm3(Predicted)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 128.037448136
• Heavy Atom Count: 10
• Complexity: 202

Purity/Quality:

97% ^*data from raw suppliers

2-Ethynylisonicotinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CC1=NC=CC(=C1)C#N

Technology Process of 2-Ethynylisonicotinonitrile

There total 3 articles about 2-Ethynylisonicotinonitrile 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: 76.0%

2-(3-hydroxy-3-methylbut-1-yn-1-yl)isonicotinonitrile (1531598-54-5) → 2-ethynylisonicotinonitrile (1211580-87-8)

Guidance literature:

With sodium hydride; In toluene; mineral oil; Dean-Stark; Reflux;

DOI:10.1016/j.bmc.2013.10.050

Reference yield: 66.0%

4-cyano-2-[2-(trimethylsilyl)ethynyl]pyridine → 2-ethynylisonicotinonitrile (1211580-87-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 0 ℃; for 2h;

Reference yield:

2-chloro-4-pyridinenitrile (33252-30-1) → 2-ethynylisonicotinonitrile (1211580-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 3 h / 60 °C

2: sodium hydride / toluene; mineral oil / Dean-Stark; Reflux

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium hydride; triethylamine; In toluene; mineral oil; 1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2013.10.050

upstream raw materials:

2-chloro-4-pyridinenitrile

2-(3-hydroxy-3-methylbut-1-yn-1-yl)isonicotinonitrile