34846-64-5

Basic information

• Product Name: 3-Cyanoquinoline
• Synonyms: 3-QUINOLINECARBONITRILE;3-CYANO-QUINOLINE;QUINOLINE-3-CARBONITRILE;3-QUINOLINECARBONITRILE HPLC 98.0% YELLOW CRYSTALLINE POWDER;3-Quinolinecarbonitrile ,98%;3-Quinolinecarbonitrile 98%
• CAS NO: 34846-64-5
• Molecular Formula: C₁₀H₆N₂
• Molecular Weight: 154.17
• EINECS: 252-248-6
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Building Blocks;Heterocyclic Building Blocks;Quinolines;Building Blocks;C8 to C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 34846-64-5.mol
• Article Data: 38

Chemical Properties

• Melting Point: 108-110 °C(lit.)
• Boiling Point: 323.7 °C at 760 mmHg
• Flash Point: 115.5 °C
• Appearance: white to light yellow crystal powder
• Density: 1.21 g/cm³
• Vapor Pressure: 0.000258mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.72±0.11(Predicted)
• CAS DataBase Reference: 3-Cyanoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyanoquinoline(34846-64-5)
• EPA Substance Registry System: 3-Cyanoquinoline(34846-64-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 34846-64-5(Hazardous Substances Data)

Usage

Description

3-Cyanoquinoline, also known as 3-Quinolinecarbonitrile, is a white to light yellow crystal powder with distinct chemical properties. It is an organic compound belonging to the quinoline family, characterized by the presence of a cyano group (-CN) at the 3rd position of the quinoline ring.

Uses

Used in Pharmaceutical Industry:
3-Cyanoquinoline is used as a template for the development of EGFR inhibitors. These inhibitors are crucial in the treatment of various types of cancer, as they target the epidermal growth factor receptor (EGFR), which is often overexpressed in cancer cells, leading to uncontrolled cell growth and proliferation.
The use of 3-Cyanoquinoline as a template allows for the design and synthesis of novel EGFR inhibitors with improved potency, selectivity, and pharmacokinetic properties. These inhibitors can potentially be used in the treatment of non-small cell lung cancer (NSCLC), head and neck cancer, and other malignancies that rely on EGFR signaling for growth and survival.

InChI:InChI=1/C10H6N2/c11-6-8-5-9-3-1-2-4-10(9)12-7-8/h1-5,7H

Upstream product

• 69875-54-3 2,4-Dichloroquinoline-3-carbonitrile 
• 5332-24-1 3-bromoquinoline 
• 544-92-3 copper(I) cyanide 
• 151-50-8 potassium cyanide 
• 79476-07-6 3-Iodoquinoline 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 143-33-9 sodium cyanide 
• 591250-21-4 2-[acetyloxymethyl(2-nitrophenyl)]acrylonitrile 
• 557-21-1 dicyanozinc 
• 552-89-6 2-nitro-benzaldehyde 
• 225237-20-7 2-(hydroxy(2-nitrophenyl)methyl)acrylonitrile 
• 557-21-1 zinc(II) cyanide 
• 612-58-8 3-methylquinoline 

Downstream Products

• 13669-42-6 3-quinolylcarboxaldehyde 
• 6480-68-8 quinoline-3-carboxylic acid 
• 70083-49-7 N-benzyl-3-cyanoquinolinium bromide 
• 87861-96-9 3-Cyano-1-(4-trifluoromethyl-benzyl)-quinolinium; bromide 
• 6480-67-7 quinoline-3-carboxamide 
• 63124-13-0 quinoline-3-carbonitrile N-oxide 
• 350249-64-8 2-[(S)-2-benzyl-1-hydroxyethyl]-1-oxo-1,2,3,4-tetrahydrobenzo[1,3-b]naphthyridine 
• 350249-63-7 2-[2-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-ethyl]-quinoline-3-carbonitrile 

Relevant articles and documents

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.