3-Nitroquinoline

Base Information

• Chemical Name: 3-Nitroquinoline
• CAS No.: 17576-53-3
• Molecular Formula: C9H6N2O2
• Molecular Weight: 174.159
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID60879658
• Nikkaji Number: J148.021I
• Wikidata: Q82861764
• ChEMBL ID: CHEMBL1501650
• Mol file: 17576-53-3.mol

Synonyms:3-Nitroquinoline;17576-53-3;Quinoline, 3-nitro-;3-nitro-quinoline;NITROQUINOLINE;Quinoline, nitro-;12408-11-6;MLS000702569;SCHEMBL2230388;CHEMBL1501650;DTXSID60879658;ZXVRNZRQQRBDLX-UHFFFAOYSA-N;HMS2509L07;MFCD00956379;AKOS006274007;SB67544;NCGC00247076-01;AS-50137;SMR000224613;LS-142070;CS-0155672;FT-0630309;O11041;A812113;AC-907/34124023

Chemical Property of 3-Nitroquinoline

Chemical Property:

• Vapor Pressure: 0.000718mmHg at 25°C
• Melting Point: 128 °C
• Refractive Index: 1.682
• Boiling Point: 317.4 °C at 760 mmHg
• PKA: 1.15±0.11(Predicted)
• Flash Point: 145.8 °C
• PSA: 58.71000
• Density: 1.354 g/cm³
• LogP: 2.66620
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 174.042927438
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

98%min ^*data from raw suppliers

3-Nitroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C=N2)[N+](=O)[O-]

Technology Process of 3-Nitroquinoline

There total 21 articles about 3-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: 99.0%

3-nitroquinoline N-oxide (7433-86-5) → 3-nitroquinoline (17576-53-3)

Guidance literature:

With 2-methyl-but-2-ene; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI); In benzene; at 30 ℃; for 15h;

DOI:10.1248/cpb.46.1656

Reference yield: 83.0%

3-aminoquinoline (580-17-6) → 3-nitroquinoline (17576-53-3)

Guidance literature:

With tert.-butylhydroperoxide; potassium iodide; In water; acetonitrile; at 80 ℃; for 6h;

DOI:10.1002/adsc.200800641

Reference yield: 74.7%

1-benzoyl-2-cyano-1,2-dihydro-3-nitroquinoline → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + 3-nitroquinoline (17576-53-3)

Guidance literature:

With hydrogenchloride; In methanol; for 14h; Heating;

DOI:10.1248/cpb.40.2262

upstream raw materials:

quinoline

3-nitroquinoline N-oxide

3-Nitro-cinchoninsaeure

3-anilino-2-nitro-acrylaldehyde

Downstream raw materials:

3-aminoquinoline

3-nitroquinoline N-oxide

3-nitro-4-aminoquinoline

3-nitro-4-methylquinoline

Refernces

• 1、 Dewar,Maitlis. "-". . p. 944,947. Retrieved 1957.
• 2、 Zhao, Jingjing,Li, Pan,Xia, Chungu,Li, Fuwei. "Metal-free regioselective C-3 nitration of quinoline N-oxides with tert-butyl nitrite". . p. 32835 - 32838. Retrieved 2015.
• 3、 Antoniak, Damian,Barbasiewicz, Micha?. "Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution". supporting information. p. 516 - 519. Retrieved 2022/01/20.
• 4、 -. "Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent". Paragraph 0084; 0085. . Retrieved 2018/09/11.