8-Bromo-6-methoxyquinoline

Base Information

• Chemical Name: 8-Bromo-6-methoxyquinoline
• CAS No.: 50488-36-3
• Molecular Formula: C10H8BrNO
• Molecular Weight: 238.084
• European Community (EC) Number: 855-652-6
• NSC Number: 130788
• DSSTox Substance ID: DTXSID90299446
• Wikidata: Q82041865
• Mol file: 50488-36-3.mol

Synonyms:8-bromo-6-methoxyquinoline;50488-36-3;MFCD11110269;NSC130788;SCHEMBL4810431;DTXSID90299446;MXMVLWCWCLMAHP-UHFFFAOYSA-N;AMY26727;AKOS015897035;NSC-130788;SB68678;AS-42979;SY265508;EN300-177918;J-519394;Z1269125113

Chemical Property of 8-Bromo-6-methoxyquinoline

Chemical Property:

• Vapor Pressure: 0.000349mmHg at 25°C
• Melting Point: 65-66 °C
• Refractive Index: 1.64
• Boiling Point: 329 °C at 760 mmHg
• PKA: 2.38±0.20(Predicted)
• Flash Point: 152.8 °C
• PSA: 22.12000
• Density: 1.516 g/cm³
• LogP: 3.00590
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 236.97893
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

99% ^*data from raw suppliers

8-Bromo-6-methoxyquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C2C(=C1)C=CC=N2)Br

Technology Process of 8-Bromo-6-methoxyquinoline

There total 7 articles about 8-Bromo-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: 75.0%

8-bromo-6-methoxy-1,2,3,4-tetrahydroquinoline (475159-35-4) → 8--bromo--6--methoxyquinoline (50488-36-3)

Guidance literature:

With diethylazodicarboxylate; In chloroform; toluene; for 12h; Sealed tube; Reflux;

DOI:10.1021/acs.orglett.0c01963

Reference yield: 61.0%

6-methoxyquinolin-8-amine (90-52-8) → 8--bromo--6--methoxyquinoline (50488-36-3)

Guidance literature:

With sodium hydroxide; copper(I) bromide; In water; hydrogen bromide; ethyl acetate;

Reference yield: 44.0%

methanol (67-56-1) + 6,8-dibromo-1,2,3,4-tetrahydroquinoline (190843-73-3) → 8--bromo--6--methoxyquinoline (50488-36-3) + 6-bromo-8-methoxy-quinoline (103028-32-6)

Guidance literature:

methanol; 6,8-dibromo-1,2,3,4-tetrahydroquinoline; With copper(l) iodide; sodium; In benzene; at 150 ℃; for 20h; Inert atmosphere;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 80 ℃; for 40h; Inert atmosphere;

DOI:10.3906/kim-1301-30

upstream raw materials:

6-methoxyquinolin-8-amine

6-methoxyquinoline N-oxide

1,2,3,4-tetrahydroisoquinoline

methanol

Downstream raw materials:

8-bromoquinolin-6-ol

8-Bromo-6-chloroquinoline

6-methoxy-N-{2-[3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethyl}-8-quinolinamine

Refernces

• 1、 Ahmad, Ashfaq,Dutta, Himangsu Sekhar,Kumar, Mohit,Khan, Afsar Ali,Raziullah,Koley, Dipankar. "Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group". . p. 5870 - 5875. Retrieved 2020/07/30.
• 2、 Oekten, Salih,Cakmak, Osman,Erenler, Ramazan,Yuece, Oenem,Tekin, Saban. "Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities". . p. 896 - 908. Retrieved 2013/12/04.