6-METHOXY-8-NITROQUINOLINE

Base Information

• Chemical Name: 6-METHOXY-8-NITROQUINOLINE
• CAS No.: 85-81-4
• Molecular Formula: C10H8 N2 O3
• Molecular Weight: 204.185
• Hs Code.: 29334900
• European Community (EC) Number: 201-633-7
• NSC Number: 1883
• UNII: ATS412O1XO
• DSSTox Substance ID: DTXSID50234050
• Nikkaji Number: J797H
• Wikidata: Q27274117
• ChEMBL ID: CHEMBL166980
• Mol file: 85-81-4.mol

Synonyms:6-Methoxy-8-nitroquinoline;8-Nitro-6-methoxyquinoline; NSC 1883

Chemical Property of 6-METHOXY-8-NITROQUINOLINE

Chemical Property:

• Appearance/Colour: YELLOW CRYSTALLINE POWDER
• Vapor Pressure: 1.97E-05mmHg at 25°C
• Melting Point: 158-160 °C(lit.)
• Refractive Index: 1.5910 (estimate)
• Boiling Point: 373.1°C at 760 mmHg
• PKA: 1.25±0.20(Predicted)
• Flash Point: 179.4°C
• PSA: 67.94000
• Density: 1.337g/cm³
• LogP: 2.67480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 204.05349212
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

6-Methoxy-8-nitroquinoline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-27-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C2C(=C1)C=CC=N2)[N+](=O)[O-]
• Uses: 6-Methoxy-8-nitroquinoline is used in treating and preventing pancreatic cancer. Also, used in preparation of Quinoline derivatives as antiparasitic agents useful in the prophylaxis and treatment of malaria and parasitic diseases.

Technology Process of 6-METHOXY-8-NITROQUINOLINE

There total 9 articles about 6-METHOXY-8-NITROQUINOLINE 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%

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) + 4-methoxy-2-nitroaniline (96-96-8) → 6-methoxy-8-nitroquinoline (85-81-4)

Guidance literature:

glycerol; 4-methoxy-2-nitroaniline; With sodium iodide; at 20 ℃; for 0.0833333h;

With sulfuric acid; for 0.166667h; Cooling with ice;

at 140 ℃; for 2h;

DOI:10.1021/acs.joc.9b00942

Reference yield: 70.0%

acrolein (107-02-8,25068-14-8) + 4-methoxy-2-nitroaniline (96-96-8) → 6-methoxy-8-nitroquinoline (85-81-4)

Guidance literature:

With hydrogenchloride; phosphoric acid; In water; at 80 - 95 ℃; for 7h; Inert atmosphere;

DOI:10.1039/c6ob01325b

Reference yield: 42.0%

4-methoxy-2-nitroaniline (96-96-8) → 6-methoxy-8-nitroquinoline (85-81-4)

Guidance literature:

With sulfuric acid; In dichloromethane; water; glycerol;

upstream raw materials:

4-methoxy-2-nitroacetanilide

glycerol

4-methoxy-2-nitroaniline

acrolein

Downstream raw materials:

6-methoxyquinolin-8-amine

6-hydroxy-8-nitroquinoline

5,7,8-trichloro-quinolin-6-ol

3,5,7,8-tetrachloro-6-methoxy-quinoline

Refernces

• 1、 Xu, Cheng,Yin, Guodong,Jia, Feng-Cheng,Wu, Yan-Dong,Wu, An-Xin. "Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage". supporting information. p. 2559 - 2564. Retrieved 2021/04/13.
• 2、 Sen, Chiranjit,Sahoo, Tapan,Singh, Harshvardhan,Suresh, Eringathodi,Ghosh, Subhash Chandra. "Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway". . p. 9869 - 9896. Retrieved 2019/08/20.