6-Bromo-2-phenylquinoline 1-oxide

Base Information

• Chemical Name: 6-Bromo-2-phenylquinoline 1-oxide
• CAS No.: 19051-07-1
• Molecular Formula: C15H10BrNO
• Molecular Weight: 300.154
• Nikkaji Number: J143.174I
• Mol file: 19051-07-1.mol

Synonyms:6-Bromo-2-phenylquinoline 1-oxide;6-bromo-1-oxido-2-phenylquinolin-1-ium;19051-07-1;Quinoline, 6-bromo-2-phenyl-, 1-oxide

Chemical Property of 6-Bromo-2-phenylquinoline 1-oxide

Chemical Property:

• Melting Point: 183 - 185 °C (ethyl acetate)
• PSA: 25.46000
• LogP: 4.69780
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 298.99458
• Heavy Atom Count: 18
• Complexity: 280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=[N+](C3=C(C=C2)C=C(C=C3)Br)[O-]

Technology Process of 6-Bromo-2-phenylquinoline 1-oxide

There total 3 articles about 6-Bromo-2-phenylquinoline 1-oxide 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: 78.0%

6-bromoquinoline-N-oxide (6563-11-7) + diphenyliodonium tetrafluoroborate → 6-bromo-2-phenylquinoline 1-oxide (19051-07-1)

Guidance literature:

With eosin; caesium carbonate; p-benzoquinone; In methanol; at -78 - 20 ℃; for 72h; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.9b02933

Reference yield: 72.0%

(E)-3-(5-bromo-2-nitrophenyl)-1-phenylprop-2-en-1-one → 6-bromo-2-phenylquinoline 1-oxide (19051-07-1)

Guidance literature:

With hydrazine hydrate; sodium hydroxide; In tetrahydrofuran; water; at 70 ℃; for 2h; Schlenk technique; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.orglett.0c04162

Reference yield: 68.0%

6-bromoquinoline-N-oxide (6563-11-7) + phenylboronic acid (98-80-6) → 6-bromo-2-phenylquinoline 1-oxide (19051-07-1)

Guidance literature:

With potassium permanganate; In acetonitrile; at 90 ℃; for 1h; regioselective reaction; Schlenk technique;

DOI:10.1016/j.cclet.2017.01.016

upstream raw materials:

6-bromoquinoline-N-oxide

phenylboronic acid

Downstream raw materials:

2-Phenyl-7-brom-benz-(1,3)-oxazepin

Refernces

• 1、 Li, Dazhi,Liang, Ce,Jiang, Zaixing,Zhang, Junzheng,Zhuo, Wang-Tao,Zou, Fan-Yue,Wang, Wan-Peng,Gao, Guo-Lin,Song, Jinzhu. "Visible-light-promoted c2 selective arylation of quinoline and pyridine n-oxides with diaryliodonium tetrafluoroborate". . p. 2733 - 2742. Retrieved 2020/03/11.