2-Chloroquinoline

Base Information

• Chemical Name: 2-Chloroquinoline
• CAS No.: 612-62-4
• Molecular Formula: C9H6ClN
• Molecular Weight: 163.606
• Hs Code.: 29334900
• European Community (EC) Number: 210-317-8
• NSC Number: 6163
• UNII: UX7RIN8GEW
• DSSTox Substance ID: DTXSID8060612
• Nikkaji Number: J95.371G
• Wikipedia: 2-Chloroquinoline
• Wikidata: Q27291324
• ChEMBL ID: CHEMBL2042580
• Mol file: 612-62-4.mol

Synonyms:2-chloroquinoline

Chemical Property of 2-Chloroquinoline

Chemical Property:

• Appearance/Colour: white to yellowish crystals, powder, chunks
• Vapor Pressure: 0.0136mmHg at 25°C
• Melting Point: 34-37 °C(lit.)
• Refractive Index: 1.652
• Boiling Point: 267.3 °C at 760 mmHg
• PKA: 0.41±0.40(Predicted)
• Flash Point: 141.2 °C
• PSA: 12.89000
• Density: 1.27 g/cm³
• LogP: 2.88820
• Storage Temp.: 0-10°C
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: Insoluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 163.0188769
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

98% ^*data from raw suppliers

2-Chloroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=N2)Cl
• Uses: 2-Chloroquinoline is an intermediate used in the synthesis of various compounds that exhibits antifungal properties. 2-Chloroquinoline is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. It reacts with benzotriazole, followed by cyclization with loss of nitrogen, gives the indolo[2,3-b]quinoline ring system for use in novel cytotoxic DNA topoisomerase II inhibitors.

Technology Process of 2-Chloroquinoline

There total 42 articles about 2-Chloroquinoline 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: 99.1%

2-hydroxyquinoline (59-31-4) → 2-Chloroquinoline (612-62-4)

Guidance literature:

With trichlorophosphate; In toluene; for 21h; Reflux; Inert atmosphere;

DOI:10.1021/acs.joc.7b02775

Reference yield: 98.0%

2-bromoquinoline (2005-43-8) → 2-Chloroquinoline (612-62-4)

Guidance literature:

With copper(I) oxide; tetramethlyammonium chloride; L-proline; In ethanol; at 110 ℃; for 10h; Inert atmosphere;

DOI:10.1039/c2cc34944b

Reference yield: 97.0%

2-Chloroquinoline 1-oxide (2423-68-9) → 2-Chloroquinoline (612-62-4)

Guidance literature:

With titanium; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1055/s-1987-28152

upstream raw materials:

phosgene

1-methyl-2-quinolin-2(1H)-one

toluene

2-quinolone

Downstream raw materials:

2-(piperidin-1-yl)quinoline

4,4-dimethylmorpholinium chloride

2-(methylthio)quinoline

2-quinolyldiphenylarsine

Refernces

• 1、 -. "Environment-friendly preparation method of 2-chloroquinoline". Paragraph 0023-0054. . Retrieved 2019/03/08.
• 2、 Stumpf, Tim-Daniel J.,Steinbach, Manfred,H?ltke, Magdalene,Heuger, Gerold,Grasemann, Franka,Fr?hlich, Roland,Schindler, Siegfried,G?ttlich, Richard. "C-Bridged Bispyrrolidines and Bispiperidines as New Ligands". . p. 5538 - 5547. Retrieved 2018/10/25.