612-62-4 Usage
Description
2-Chloroquinoline is an organic compound characterized by its white to yellowish crystalline, powdery, or chunky appearance. It is a chlorinated derivative of quinoline, which is a tricyclic aromatic compound with a broad range of applications in various industries.
Uses
Used in Pharmaceutical Industry:
2-Chloroquinoline is used as an intermediate in the synthesis of various compounds, particularly those with antifungal properties. It plays a crucial role in the development of new drugs to combat fungal infections.
Used in Organic Synthesis:
2-Chloroquinoline serves as an important raw material and intermediate in organic synthesis, where it is utilized to create a variety of chemical compounds with diverse applications.
Used in Agrochemicals:
In the agrochemical industry, 2-Chloroquinoline is employed as a key intermediate for the production of various pesticides and other agricultural chemicals, contributing to the development of more effective and environmentally friendly products.
Used in Dye Industry:
2-Chloroquinoline is also used as an intermediate in the synthesis of dyes, where its unique chemical properties enable the creation of a wide range of colors and pigments for various applications.
Used in Cytotoxic DNA Topoisomerase II Inhibitors:
2-Chloroquinoline is used as a starting material in the synthesis of novel cytotoxic DNA topoisomerase II inhibitors. It reacts with benzotriazole and undergoes cyclization with the loss of nitrogen, resulting in the formation of the indolo[2,3-b]quinoline ring system, which is essential for the development of these inhibitors. These inhibitors have potential applications in cancer treatment, as they can interfere with the replication and transcription of DNA in cancer cells, thereby inhibiting their growth and proliferation.
Synthesis Reference(s)
The Journal of Organic Chemistry, 67, p. 7884, 2002 DOI: 10.1021/jo016196iSynthesis, p. 1013, 1987 DOI: 10.1055/s-1987-28152
Purification Methods
Purify it by crystallisation of its picrate to constant melting point (123-124o) from *benzene, regenerating the base and distilling it under vacuum [Cumper et al. J Chem Soc 1183 1962]. 2-Chloroquinoline can be crystallised from EtOH. Its picrate has m 123-124o (from EtOH). [Beilstein 20 H 359, 20/7 V 312.]
Check Digit Verification of cas no
The CAS Registry Mumber 612-62-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 2 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 612-62:
(5*6)+(4*1)+(3*2)+(2*6)+(1*2)=54
54 % 10 = 4
So 612-62-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H6ClN/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
612-62-4Relevant articles and documents
Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
supporting information, p. 146 - 153 (2020/03/10)
The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
Environment-friendly preparation method of 2-chloroquinoline
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Paragraph 0023-0054, (2019/03/08)
The invention discloses an environment-friendly preparation method of 2-chloroquinoline. The method comprises the following steps: dissolving quinoline N-oxide as a raw material in a certain amount ofa solvent, adding inorganic salt, a cocatalyst, organic alkali and a phase transfer catalyst to form a raw material system, controlling to form a proper temperature, dissolving bis(trichloromethyl)carbonate in a certain amount of the organic solvent to obtain a mixture, slowly dropwise adding the mixture into the raw material system for reaction, and after the reaction is finished, carrying out column chromatography isolation, so as to obtain 2-chloroquinoline. The preparation method is simple, the reaction period is short, and a phosphorus-containing reagent and heavy metals are not adopted;and compared with the prior art, the method has the advantages that the environmental pollution is low, the operation is safe, and the cost is low. The method is applied to the environment-friendly chlorination reaction of quinoline N-oxide and is not limited to the preparation of 2-chloroquinoline.
C-Bridged Bispyrrolidines and Bispiperidines as New Ligands
Stumpf, Tim-Daniel J.,Steinbach, Manfred,H?ltke, Magdalene,Heuger, Gerold,Grasemann, Franka,Fr?hlich, Roland,Schindler, Siegfried,G?ttlich, Richard
, p. 5538 - 5547 (2018/10/25)
The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.