2-Chloro-5-nitroquinoline

Base Information

• Chemical Name: 2-Chloro-5-nitroquinoline
• CAS No.: 13067-94-2
• Molecular Formula: C9H5ClN2O2
• Molecular Weight: 208.604
• Hs Code.: 2933499090
• NSC Number: 261562
• DSSTox Substance ID: DTXSID60312772
• Wikidata: Q82063499
• ChEMBL ID: CHEMBL2042582
• Mol file: 13067-94-2.mol

Synonyms:Quinoline, 2-chloro-5-nitro-;2-chloro-5-nitroquinoline;

Chemical Property of 2-Chloro-5-nitroquinoline

Chemical Property:

• Vapor Pressure: 8.18E-05mmHg at 25°C
• Boiling Point: 351.7°Cat760mmHg
• Flash Point: 166.5°C
• PSA: 58.71000
• Density: 1.484g/cm³
• LogP: 3.31960
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Methanol, Ethyl Acetate
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 208.0039551
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-Chloro-5-nitroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=N2)Cl)C(=C1)[N+](=O)[O-]
• Uses: 2-Chloro-5-nitroquinoline is used in the synthesis of potent, orally active corticotropin-releasing factor-1 receptor antagonists.

Technology Process of 2-Chloro-5-nitroquinoline

There total 9 articles about 2-Chloro-5-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%

5-nitro-2<1H>quinolinone (6938-27-8) → 2-chloro-5-nitroquinoline (13067-94-2)

Guidance literature:

With trichlorophosphate; In 1,2-dichloro-ethane; at 80 ℃; for 12h;

DOI:10.1016/j.ejmech.2018.03.023

Reference yield: 54.0%

2-Chloroquinoline (612-62-4) → 2-chloro-5-nitroquinoline (13067-94-2) + 2-chloro-8-nitroquinoline (4225-86-9)

Guidance literature:

2-Chloroquinoline; With sulfuric acid; nitric acid; at 0 - 20 ℃; for 1h;

With sodium carbonate; In water;

DOI:10.1016/j.ejmech.2012.04.029

Reference yield: 46.0%

5-nitro-quinoline-1-oxide (7613-19-6) → 2-chloro-5-nitroquinoline (13067-94-2)

Guidance literature:

With trichloroacetonitrile; triphenylphosphine; In toluene; at 115 ℃; for 4h; regioselective reaction; Sealed tube;

DOI:10.1002/ejoc.201501567

upstream raw materials:

2-Chloroquinoline

5-nitro-quinoline-1-oxide

5-nitroquinolin-2-ol

phosphorus pentachloride

Downstream raw materials:

5-nitro-[2]quinolylamine

5-nitro-2<1H>quinolinone

2-chloro-5-aminoquinoline

2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-5-nitroquinoline

Refernces

• 1、 Pedron, Julien,Boudot, Clotilde,Hutter, Sébastien,Bourgeade-Delmas, Sandra,Stigliani, Jean-Luc,Sournia-Saquet, Alix,Moreau, Alain,Boutet-Robinet, Elisa,Paloque, Lucie,Mothes, Emmanuelle,Laget, Michèle,Vendier, Laure,Pratviel, Geneviève,Wyllie, Susan,Fairlamb, Alan,Azas, Nadine,Courtioux, Bertrand,Valentin, Alexis,Verhaeghe, Pierre. "Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study". . p. 135 - 152. Retrieved 2018.
• 2、 Thorat, Shivaji A.,Lee, Yoonji,Jung, Aeran,Ann, Jihyae,Ahn, Songyeon,Baek, Jisoo,Zuo, Dongxu,Do, Nayeon,Jeong, Jin Ju,Blumberg, Peter M.,Esch, Timothy E.,Turcios, Noe A.,Pearce, Larry V.,Ha, Hee-Jin,Yoo, Young Dong,Hong, Sunhye,Choi, Sun,Lee, Jeewoo. "Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift". . p. 370 - 384. Retrieved 2021/02/05.