5-CHLOROQUINOLINE Chemical Properties

Melting point:

28-32 °C

Boiling point:

263°C(lit.)

Density 

1.2108 (rough estimate)

refractive index 

1.6110 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform, Ethyl Acetate, Methanol

form 

Solid

pka

3.88±0.12(Predicted)

color 

Off-White to Yellow

λmax

317nm(EtOH aq.)(lit.)

BRN 

114722

InChI

InChI=1S/C9H6ClN/c10-8-4-1-5-9-7(8)3-2-6-11-9/h1-6H

InChIKey

HJSRGOVAIOPERP-UHFFFAOYSA-N

SMILES

N1C2C(=C(Cl)C=CC=2)C=CC=1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

5-CHLOROQUINOLINE Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

5-Chloroquinoline (cas# 635-27-8) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 5-chloroquinoline from 5-aminoquinoline: 5-aminoquinoline (756 mg, 5.24 mmol) was suspended in an aqueous 2N HCl solution (31 mL) and cooled to 0°C. A solution of NaNO2 (470 mg, 6.80 mmol) in water (14 mL) was added slowly with stirring. The reaction mixture was kept stirred at 0 °C for 30 min. Subsequently, a concentrated hydrochloric acid solution of CuCl (644 mg, 6.51 mmol) was added and additional concentrated hydrochloric acid (16 mL) was added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 24 hours. After the reaction was completed, saturated NaHCO3 solution was added slowly until no more gas was produced. The organic phase was extracted with dichloromethane (3 x 50 mL) and the combined organic layers were washed with brine and dried over anhydrous MgSO4. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: EtOAc/hexane=1:1) to afford the target product 5-chloroquinoline (579 mg, 68% yield).

References

[1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2611 - 2623
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[3] Patent: WO2016/86200, 2016, A1. Location in patent: Page/Page column 235

5-CHLOROQUINOLINE(635-27-8)Related Product Information

• Quinclorac
• 5-Chloroquinolin-2-aMine
• 5-chloroquinolin-3-aMine
• 5-Chloroquinoxaline
• 5-CHLOROQUINOLINE-8-CARBOXYLIC ACID
• 5-Chloroquinazoline
• 5-Chloroquinoline-3-carboxylic acid ethyl ester
• 5-Chloroquinoline-2-carboxylic acid
• 5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID
• Clioquinol
• 5,7-Dichloro-8-hydroxyquinoline
• 5,7-Dichloro-8-hydroxyquinaldine
• 5-Chloro-8-hydroxyquinoline
• 5-CHLORO-2,8-DIMETHYL-4-QUINOLINOL
• 2-CHLOROQUINOLINE-3-CARBALDEHYDE
• 4-Chloroquinoline-3-boronic acid, 97%
• 4-chloroquinoline-6-carboxylic acid
• ETHYL 4-CHLOROQUINOLINE-2-CARBOXYLATE