555155-04-9

Basic information

• Product Name: 2-(quinolin-5-yl)acetonitrile
• Synonyms: 2-(quinolin-5-yl)acetonitrile
• CAS NO: 555155-04-9
• Molecular Formula: C11H8N2
• Molecular Weight: 168.19
• Mol File: 555155-04-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 350.5±17.0 °C(Predicted)
• Appearance: /
• Density: 1.176±0.06 g/cm3(Predicted)
• PKA: 4.41±0.12(Predicted)
• CAS DataBase Reference: 2-(quinolin-5-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(quinolin-5-yl)acetonitrile(555155-04-9)
• EPA Substance Registry System: 2-(quinolin-5-yl)acetonitrile(555155-04-9)

Safety Data

• Hazardous Substances Data: 555155-04-9(Hazardous Substances Data)

Usage

General Description

2-(quinolin-5-yl)acetonitrile, also known as 5-cyanoquinolin-2-yl)acetonitrile, is a chemical compound with the molecular formula C12H8N2. It is a nitrile derivative of quinoline, characterized by a quinoline ring with a cyano group attached at the 5-position and a acetonitrile group at the 2-position. 2-(quinolin-5-yl)acetonitrile is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Its chemical structure and properties make it a valuable building block for the development of new drug molecules and organic synthesis. Additionally, 2-(quinolin-5-yl)acetonitrile is known for its potential biological activities and has been studied for its pharmacological properties.

Upstream product

• 773837-37-9 sodium cyanide 
• 110333-07-8 5-(chloromethyl)quinoline 
• 16178-42-0 quinolin-5-ylmethanol 
• 22934-41-4 quinoline-5-carbaldehyde 
• 2942-58-7 diethyl cyanophosphonate 

Relevant articles and documents

Discovery of pyridyl-based inhibitors of Plasmodium falciparum N-myristoyltransferase

N-Myristoyltransferase (NMT) represents an attractive drug target in parasitic infections such as malaria due to its genetic essentiality and amenability to inhibition by drug-like small molecules. Scaffold simplification from previously reported inhibitors containing bicyclic cores identified phenyl derivative 3, providing a versatile platform to study the effects of substitution on the scaffold, which yielded pyridyl 19. This molecule exhibited improved enzyme and cellular potency, and reduced lipophilicity compared to inhibitor 3. Further structure-based inhibitor design led to the discovery of 30, the most potent inhibitor in this series, which showed single-digit nM enzyme affinity and sub-μM anti-plasmodial activity.

An improved method for direct conversion of heteroaryl-aldehydes to heteroaryl-acetonitriles

Treatment of heteroaryl-aldehydes with diethyl cyanophosphonate in the presence of a catalytic amount of LiCN affords phosphorylated cyanohydrins which are reduced in situ with SmI2 to give heteroaryl-acetonitriles in generally good overall yields (50-100%). The generality of the process is demonstrated.