103983-94-4

Basic information

• Product Name: 2-(quinolin-6-yl)acetonitrile
• Synonyms: 2-(quinolin-6-yl)acetonitrile
• CAS NO: 103983-94-4
• Molecular Formula: C₁₁H₈N₂
• Molecular Weight: 0
• Mol File: 103983-94-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(quinolin-6-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(quinolin-6-yl)acetonitrile(103983-94-4)
• EPA Substance Registry System: 2-(quinolin-6-yl)acetonitrile(103983-94-4)

Safety Data

• Hazardous Substances Data: 103983-94-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(quinolin-6-yl)acetonitrile is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its presence in the molecular structure of these drugs contributes to their therapeutic properties and efficacy.
Used in Agrochemical Production:
In the agrochemical sector, 2-(quinolin-6-yl)acetonitrile serves as a key intermediate in the production of pesticides and other crop protection agents. Its incorporation enhances the effectiveness of these chemicals in protecting crops from pests and diseases.
Used in Organic Synthesis:
2-(quinolin-6-yl)acetonitrile is utilized as a building block in organic synthesis for the preparation of heterocyclic compounds. Its unique structure and reactivity allow for the creation of a wide range of complex organic molecules with diverse applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(quinolin-6-yl)acetonitrile is employed as a versatile reagent for the development of new pharmaceutical compounds. Its ability to form various chemical bonds and its compatibility with different molecular frameworks make it an essential component in drug discovery and design processes.

Upstream product

• 2644-82-8 6-(chloromethyl)quinoline 
• 151-50-8 potassium cyanide 
• 5332-25-2 6-bromoquinoline 
• 105-56-6 ethyl 2-cyanoacetate 
• 612-57-7 6-chloroquinoline 
• 100516-88-9 6-(hydroxymethyl)quinoline 
• 18293-53-3 2-trimethylsilylacetonitrile 

Relevant articles and documents

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

Design, synthesis, and biological evaluation of novel imidazo[1,2-a]pyridine derivatives as potent c-met inhibitors

A series of imidazo[1,2-a]pyridine derivatives against c-Met was designed by means of bioisosteric replacement. In this study, a selective, potent c-Met inhibitor, 22e was identified, with IC50 values of 3.9 nM against c-Met kinase and 45.0 nM