5-Chloro-8-hydroxyquinoline Chemical Properties

Melting point:

122-124 °C(lit.)

Boiling point:

348.7±22.0 °C(Predicted)

Density 

1.2364 (rough estimate)

vapor pressure 

0.003Pa at 25℃

refractive index 

1.5330 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

0.019g/l (experimental)

form 

Powder

pka

3.77±0.10(Predicted)

color 

Light green to gray

Sensitive 

Light Sensitive

Merck 

14,2422

BRN 

5289

InChIKey

RWPWQYXFGFYJBA-UHFFFAOYSA-N

CAS DataBase Reference

130-16-5(CAS DataBase Reference)

NIST Chemistry Reference

8-Quinolinol, 5-chloro-(130-16-5)

EPA Substance Registry System

8-Quinolinol, 5-chloro- (130-16-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

VC4590000

TSCA 

Yes

HS Code 

29334990

MSDS

• Language:English Provider:Cloxiquine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Chloro-8-hydroxyquinoline Usage And Synthesis

Chemical Properties

light green to grey powder

Uses

antibacterial, antifungal

Uses

Dermofungin, is an impurity of Cioquinol, which is an antifungal and antiprotozoal drug.

Definition

ChEBI: Cloxiquine is a member of quinolines and an organochlorine compound.

Synthesis Reference(s)

The Journal of Organic Chemistry, 70, p. 8590, 2005 DOI: 10.1021/jo051191x

Synthesis

GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to a round-bottomed flask containing 4-chloro-2-aminophenol (~1 mmol). Acrolein diethyl acetal (2.5 mmol) was added to the reaction mixture. The resulting solution was refluxed at 111°C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized to pH 7-8 with solid Na2CO3. Subsequently, the product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined and dried with anhydrous Na2SO4. After removal of solvent by evaporation under reduced pressure, the crude product was purified by column chromatography with the eluent being a mixture of 15% ethyl acetate/cyclohexane and methanol to afford the target compound 5-chloro-8-hydroxyquinoline.

in vitro

Cloxiquine (cloxyquin) exhibits antituberculosis activities, with MICs ranging from 0.062 to 0.25 μg/mL against 9 standard strains and 150 Mycobacterium tuberculosis .
Cloxiquine (0.5-10 μM; 24 h) suppresses both B16F10 and A375 cell growth in a dose-dependent manner.|
Cloxiquine (0.5-10 μM; 24 h) inhibits the migration of B16F10 and A375 cells.
Cloxiquine (0.5-2.5 μM; 24 h) suppresses glycolysis in B16F10 cells.

in vivo

Cloxiquine (5-25 mg/kg; i.p. daily for 8 d) suppresses tumor growth in a mouse B16F10 melanoma xenograft model.
Cloxiquine (5-25 mg/kg; i.p. daily for 14 d) suppresses tumor metastasis in mouse B16F10 melanoma lung metastatic model.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439

5-Chloro-8-hydroxyquinoline(130-16-5)Related Product Information

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