2-Chloroquinoline Chemical Properties

Melting point:

34-37 °C (lit.)

Boiling point:

266-267 °C (lit.)

Density 

1.23 g/mL at 25 °C (lit.)

refractive index 

1.6342 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

form 

Crystalline Powder, Crystals and/or Chunks or Fused Mass

pka

0.41±0.40(Predicted)

color 

White to yellow

Water Solubility 

Insoluble

BRN 

112561

InChI

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

InChIKey

OFUFXTHGZWIDDB-UHFFFAOYSA-N

SMILES

Clc1ccc2ccccc2n1

CAS DataBase Reference

612-62-4(CAS DataBase Reference)

NIST Chemistry Reference

Quinoline, 2-chloro-(612-62-4)

EPA Substance Registry System

Quinoline, 2-chloro- (612-62-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

VB2320000

F 

8

TSCA 

TSCA listed

HS Code 

29334900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:2-Chloroquinoline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloroquinoline Usage And Synthesis

Chemical Properties

white to yellowish crystals, powder, chunks or

Uses

2-Chloroquinoline is an intermediate used in the synthesis of various compounds that exhibits antifungal properties.

Uses

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 67, p. 7884, 2002 DOI: 10.1021/jo016196i
Synthesis, p. 1013, 1987 DOI: 10.1055/s-1987-28152

Synthesis

In a dry four-necked reaction flask add 20mL of dichloromethane, add 2.175g (15mmol) of quinoline N-oxide, turn on the stirring, cool to 0??C add 3.035g (30mmol) of triethylamine, the temperature of the system is controlled below -5??C, add 0.438g (7.5mmol) of sodium chloride, 1.305g (0.75mmol) of sodium conidiosulfate and 0.136g (0.6mmol) benzyltriethylammonium chloride, continue to lower the temperature to below -10 ??, dropwise add 8mL of dichloromethane solution containing 2.222g (7.5mmol) bis (trichloromethyl) carbonate, and the reaction was carried out at this temperature for 6h. At the end of the reaction, the reaction was quenched by adding 10mL of deionized water, the layers were separated and the organic phase was washed with 10mL of a 10% sodium hydroxide solution, then with 10mL of deionized water, and the organic phase was washed with 10mL of 10% sodium hydroxide solution. The organic phase was washed with 10 mL of 10% sodium hydroxide solution, then washed with 10 mL of deionized water, and finally the aqueous phase was extracted with (15 mL*2) dichloromethane, and the organic layers were combined, dried with anhydrous MgSO4, and concentrated to obtain the crude product. After purification by column chromatography, 1.501g of product was obtained with 61.4% yield.

Purification Methods

Purify it by crystallisation of its picrate to constant melting point (123-124o) from *benzene, regenerating the base and distilling it under vacuum [Cumper et al. J Chem Soc 1183 1962]. 2-Chloroquinoline can be crystallised from EtOH. Its picrate has m 123-124o (from EtOH). [Beilstein 20 H 359, 20/7 V 312.]

2-Chloroquinoline(612-62-4)Related Product Information

• CHLOROQUINE
• quinolinium hydrogen sulphate
• Quinhydrone
• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• 8-Hydroxyquinoline
• Isoquinoline
• 4-Chloroquinoline
• Ethoxyquin
• Quinclorac
• 7-CHLOROQUINOLINE
• 2-CHLOROQUINOLINE-4-CARBOXYLIC ACID
• 6-BROMO-2-CHLOROQUINOLINE-4-CARBONYL CHLORIDE
• 2-CHLOROQUINOLINE-3-CARBALDEHYDE
• 6-BROMO-2-CHLOROQUINOLINE-4-CARBOXYLIC ACID, 97
• 2-CHLORO-6-METHOXYQUINOLINE-3-CARBALDEHYDE
• 2-CHLOROLEPIDINE
• 2-Chloro-3-methylquinoline
• 8-Chloroquinoline ,99%