6-Nitroquinoline

Base Information

• Chemical Name: 6-Nitroquinoline
• CAS No.: 613-50-3
• Molecular Formula: C9H6N2O2
• Molecular Weight: 174.159
• Hs Code.: 29339900
• European Community (EC) Number: 210-346-6
• NSC Number: 4141
• UNII: 7033583N3J
• DSSTox Substance ID: DTXSID1020984
• Nikkaji Number: J2.997A
• Wikidata: Q27265819
• ChEMBL ID: CHEMBL353078
• Mol file: 613-50-3.mol

Synonyms:6-Nitroquinoline;613-50-3;QUINOLINE, 6-NITRO-;6-Nitro-quinoline;CCRIS 456;NSC 4141;EINECS 210-346-6;MFCD00006799;BRN 0136138;AI3-08863;DTXSID1020984;UNII-7033583N3J;NSC-4141;7033583N3J;5-20-07-00326 (Beilstein Handbook Reference);6-nitro quinoline;NSC4141;6-Nitroquinoline, 98%;NITROQUINOLINE, 6-;Oprea1_316994;Oprea1_756562;DTXCID70984;SCHEMBL366012;CHEMBL353078;AMY23304;BCP27373;STR06205;Tox21_200508;BBL034646;STL426671;AKOS000131406;AC-5110;CS-W017512;LS-7561;SB67571;NCGC00248666-01;NCGC00258062-01;CAS-613-50-3;SY008973;FT-0621280;N0252;EN300-86243;A15691;AC-907/25014227;SR-01000473458;J-200080;SR-01000473458-1;Q27265819;F0848-0299

Chemical Property of 6-Nitroquinoline

Chemical Property:

• Appearance/Colour: beige to light brown powder
• Vapor Pressure: 0.000233mmHg at 25°C
• Melting Point: 151-153 °C(lit.)
• Refractive Index: 1.682
• Boiling Point: 335.4 °C at 760 mmHg
• PKA: 3.24±0.10(Predicted)
• Flash Point: 156.7 °C
• PSA: 58.71000
• Density: 1.354 g/cm³
• LogP: 2.66620
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble in water
• XLogP3: 1.8
• 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:

99% ^*data from raw suppliers

6-Nitroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 7-22-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC2=C(C=CC(=C2)[N+](=O)[O-])N=C1

Technology Process of 6-Nitroquinoline

There total 25 articles about 6-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: 97.0%

6-chloroquinoline (612-57-7) → 6-nitroquinoline (613-50-3)

Guidance literature:

With Tris(3,6-dioxaheptyl)amine; sodium nitrite; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; In tert-butyl alcohol; at 130 ℃; for 24h; Product distribution / selectivity; Inert atmosphere;

Reference yield: 94.0%

quinolin-6-yl triflate (173089-80-0) → 6-nitroquinoline (613-50-3)

Guidance literature:

With Tris(3,6-dioxaheptyl)amine; sodium nitrite; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; In tert-butyl alcohol; at 130 ℃; for 24h; Product distribution / selectivity; Inert atmosphere;

Reference yield: 91.0%

6-nitro-1,2,3,4-tetrahydroquinoline (14026-45-0) → 6-nitroquinoline (613-50-3)

Guidance literature:

With perylene diimide covalent immobilized to SiO₂ nanospheres; air; In N,N-dimethyl acetamide; at 20 ℃; UV-irradiation;

DOI:10.1002/ejoc.202000170

upstream raw materials:

quinoline

4-nitro-aniline

glycerol

N-(4-Nitrophenyl)acetamide

Downstream raw materials:

1-methyl-6-nitro-quinolinium; iodide

6-aminoquinoline

6-amino-1,2,3,4-tetrahydroquinoline

6-nitroquinolin-2-ol

Refernces

• 1、 An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee. "Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents". supporting information. p. 2876 - 2894. Retrieved 2021/02/01.
• 2、 Su, Chenliang,Yu, Kunyi,Zhang, Hanjie,Zhu, Yongfa. "Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions". supporting information. p. 1956 - 1960. Retrieved 2020/04/10.