2-Chloro-6-methoxyquinoline

Base Information

• Chemical Name: 2-Chloro-6-methoxyquinoline
• CAS No.: 13676-02-3
• Molecular Formula: C10H8ClNO
• Molecular Weight: 193.633
• Hs Code.: 2933499090
• European Community (EC) Number: 237-162-9
• UNII: J6R5UCC53B
• DSSTox Substance ID: DTXSID10159912
• Nikkaji Number: J277.979J
• Wikidata: Q72453518
• Mol file: 13676-02-3.mol

Synonyms:2-Chloro-6-methoxyquinoline;13676-02-3;2-Chloro-6-methoxy-quinoline;QUINOLINE, 2-CHLORO-6-METHOXY-;J6R5UCC53B;EINECS 237-162-9;MFCD00799212;UNII-J6R5UCC53B;SCHEMBL483893;DTXSID10159912;STK008155;6-METHOXY-2-CHLORO-QUINOLINE;AKOS005067594;AB07225;CS-W008577;FS-3348;2-Chloro-6-methoxyquinoline, AldrichCPR;SY101758;AM20050800;FT-0611873;EN300-50888;A807124;F2167-1297

Chemical Property of 2-Chloro-6-methoxyquinoline

Chemical Property:

• Vapor Pressure: 0.0011mmHg at 25°C
• Melting Point: 106-107℃
• Refractive Index: 1.621
• Boiling Point: 310.469 °C at 760 mmHg
• Flash Point: 141.567 °C
• PSA: 22.12000
• Density: 1.268 g/cm³
• LogP: 2.89680
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 193.0294416
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-6-methoxyquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)N=C(C=C2)Cl

Technology Process of 2-Chloro-6-methoxyquinoline

There total 12 articles about 2-Chloro-6-methoxyquinoline 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: 87.0%

6-methoxyquinoline N-oxide (6563-13-9) → 2-chloro-6-methoxyquinoline (13676-02-3) + 4-chloro-6-methoxyquinoline (4295-04-9)

Guidance literature:

6-methoxyquinoline N-oxide; With tetrabutyl-ammonium chloride; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

With p-toluenesulfonylanhydride; In dichloromethane; at 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol3034675

Reference yield: 86.0%

6-methoxy-quinolin-2-ol (13676-00-1) → 2-chloro-6-methoxyquinoline (13676-02-3)

Guidance literature:

With trichlorophosphate; for 2h; Reflux;

Reference yield: 73.0%

6-methoxyquinoline N-oxide (6563-13-9) → 2-chloro-6-methoxyquinoline (13676-02-3)

Guidance literature:

With trichloroacetonitrile; triphenylphosphine; In toluene; at 115 ℃; for 4h; regioselective reaction; Sealed tube;

DOI:10.1002/ejoc.201501567

upstream raw materials:

6-methoxy-quinolin-2-ol

6-Methoxy-1-methyl-2-oxo-1,2-dihydroquinoline

6-methoxy-2(1H)-quinolinone

3-(4-methoxyphenyl)-N-(4-methoxyphenyl)prop-(2E)-enamide

Downstream raw materials:

2-amino-6-methoxy quinoline

N²-(6-methoxy-[2]quinolyl)-N¹,N¹,N³,N³-tetramethyl-propane-1,2,3-triyltriamine

6-hydroxy-2-chloroquinoline

6-Methoxy-quinoline-2-carboxylic acid

Refernces

• 1、 Sugimoto, Osamu,Iwasaki, Hyuma,Tanji, Ken-Ichi. "Development of a facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines". . p. 1445 - 1454. Retrieved 2015.
• 2、 Wengryniuk, Sarah E.,Weickgenannt, Andreas,Reiher, Christopher,Strotman, Neil A.,Chen, Ke,Eastgate, Martin D.,Baran, Phil S.. "Regioselective bromination of fused heterocyclic N-oxides". supporting information. p. 792 - 795. Retrieved 2013/04/10.