2-Chloro-4-methylquinoline

Base Information

• Chemical Name: 2-Chloro-4-methylquinoline
• CAS No.: 634-47-9
• Molecular Formula: C10H8ClN
• Molecular Weight: 177.633
• Hs Code.: 29334900
• European Community (EC) Number: 211-209-3
• NSC Number: 96476
• UNII: 2U5ATH9EJR
• DSSTox Substance ID: DTXSID00212808
• Nikkaji Number: J95.797F
• Wikidata: Q72455187
• Mol file: 634-47-9.mol

Synonyms:2-Chloro-4-methylquinoline;634-47-9;2-Chlorolepidine;Quinoline, 2-chloro-4-methyl-;2-chloro-4-methyl-quinoline;Lepidine, 2-chloro-;C10H8ClN;MFCD00006742;2U5ATH9EJR;EINECS 211-209-3;NSC 96476;NSC-96476;NSC96476;UNII-2U5ATH9EJR;2-chloro-4methylquinoline;SCHEMBL832589;DTXSID00212808;HMS1717C20;2-Chloro-4-methylquinoline, 99%;AMY15540;BCP33185;BBL010332;STK384955;AKOS000268283;4N-501S;CS-W017357;SB67543;NCGC00186368-01;NCGC00186368-02;AC-25670;SY035548;FT-0611786;EN300-17749;AE-848/06107050;Z57012199;F1244-0147

Chemical Property of 2-Chloro-4-methylquinoline

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0026mmHg at 25°C
• Melting Point: 55-58 °C(lit.)
• Refractive Index: 1.634
• Boiling Point: 296 °C at 760 mmHg
• PKA: 0.98±0.50(Predicted)
• Flash Point: 158.2 °C
• PSA: 12.89000
• Density: 1.225 g/cm³
• LogP: 3.19660
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 177.0345270
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-4-methyl-quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=NC2=CC=CC=C12)Cl
• Description: 4-Methyl-2-chloro-quinoline is an organic intermediate. It has been reported that it can be used to prepare graphite electrodes based on CrO-FeO-PbO and quinoline modified and a modified vermiculite adsorbent for the adsorption and removal of benzene in chemical wastewater.
• Uses: 2-Chloro-4-methyl-quinoline is a useful synthetic intermediate. It is an intermediate used to synthesize 4-Methyl-2-(1-piperidinyl)-quinoline (M320715) which is a potent inhibitor of TRPC4 channels, responsible for various stimulation, muscle response due to interaction with the environment. 2-Chloro-4-methyl-quinoline is also considered as a cyanine dye.

Technology Process of 2-Chloro-4-methylquinoline

There total 15 articles about 2-Chloro-4-methylquinoline 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: 96.0%

4-methylquinolin-2-ol (607-66-9,84909-43-3) → 2-chloro-4-methylquinoline (634-47-9)

Guidance literature:

With phosphorus pentachloride; trichlorophosphate; for 24h; Heating;

DOI:10.1016/S1383-5718(99)00226-0

Reference yield: 82.0%

2-Chloro-4-methylquinoline 1-oxide (10286-18-7) → 2-chloro-4-methylquinoline (634-47-9)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate; In acetonitrile; at 20 ℃; for 0.0833333h; chemoselective reaction; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.0c02805

Reference yield: 81.0%

4-methylquinoline 1-oxide (4053-40-1) → 2-chloro-4-methylquinoline (634-47-9)

Guidance literature:

With trichlorophosphate; In dichloromethane; N,N-dimethyl-formamide; at 0 - 25 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.11.005

upstream raw materials:

4-methylquinolin-2-ol

benzoyl chloride

2-chloro-4-methyl-7-aminoquinoline

4-methyl-1,2-dihydroquinolin-2-one

Downstream raw materials:

4-methyl-2-(4-morpholinyl)quinoline

4-methyl-2-(piperazin-1-yl)quinoline

4-methyl-2-(4-methylpiperazin-1-yl)quinoline

2-(4-ethoxy-phenoxy)-4-methyl-quinoline

Refernces

• 1、 Azad, Rajaram,Karnik, Kshipra S.,Sarkate, Aniket P.,Tiwari, Shailee V.,Wakte, Pravin S.. "Free energy perturbation guided Synthesis with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)". . . Retrieved 2021/08/09.
• 2、 Alegre-Requena, Juan V.,Levy, Jeffrey N.,Liu, Renrong,McNally, Andrew,Paton, Robert S.. "Selective Halogenation of Pyridines Using Designed Phosphine Reagents". supporting information. p. 11295 - 11305. Retrieved 2020/07/13.