6-Methyl-8-nitroquinoline

Base Information

• Chemical Name: 6-Methyl-8-nitroquinoline
• CAS No.: 68420-92-8
• Molecular Formula: C10H8N2O2
• Molecular Weight: 188.186
• Hs Code.: 2933499090
• NSC Number: 74535
• DSSTox Substance ID: DTXSID1071531
• Nikkaji Number: J149.664F
• Wikidata: Q81999201
• Mol file: 68420-92-8.mol

Synonyms:6-Methyl-8-nitroquinoline;68420-92-8;Quinoline, 6-methyl-8-nitro-;6-methyl-8-nitro-quinoline;NSC74535;SCHEMBL2472343;DTXSID1071531;NSC 74535;NSC-74535;AKOS006320732

Chemical Property of 6-Methyl-8-nitroquinoline

Chemical Property:

• Vapor Pressure: 0.00013mmHg at 25°C
• Boiling Point: 344.6°Cat760mmHg
• Flash Point: 162.2°C
• PSA: 58.71000
• Density: 1.298g/cm³
• LogP: 2.97460
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 188.058577502
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

98.5% ^*data from raw suppliers

6-Methyl-8-nitroquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1)[N+](=O)[O-])N=CC=C2

Technology Process of 6-Methyl-8-nitroquinoline

There total 5 articles about 6-Methyl-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: 85.0%

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) + 4-methyl-2-nitroaniline (89-62-3) → 6-methyl-8-nitroquinoline (68420-92-8)

Guidance literature:

glycerol; 4-methyl-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: 69.0%

6-bromo-8-nitroquinoline (68527-67-3) + Trimethylboroxine (823-96-1) → 6-methyl-8-nitroquinoline (68420-92-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.01.003

Reference yield:

acrolein (107-02-8,25068-14-8) + 4-methyl-2-nitroaniline (89-62-3) → 6-methyl-8-nitroquinoline (68420-92-8)

Guidance literature:

With hydrogenchloride; phosphoric acid; In water; at 80 - 95 ℃; for 4h;

DOI:10.1002/ejoc.201800389

upstream raw materials:

glycerol

4-methyl-2-nitroaniline

4-Bromo-2-nitroaniline

6-bromo-8-nitroquinoline

Downstream raw materials:

5-methyl-1,10-phenanthroline

6-Methyl-8-hydroxyquinoline

8-amino-6-methylquinoline

Refernces

• 1、 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.
• 2、 Chen, Hao,Li, Pinhua,Wang, Min,Wang, Lei. "Transition-Metal-Free Regioselective C–H Bond Fluorination of 8-Amidoquinolines with Selectfluor". supporting information. p. 2091 - 2097. Retrieved 2018/05/31.