| Identification | More | [Name]
5-Chloro-8-hydroxyquinoline | [CAS]
130-16-5 | [Synonyms]
5-CHLORO-8-HYDROXYQUINOLINE
5-CHLORO-8-QUINOLINOL
5-CHLOROOXINE
5-CHLOROQUINOPHENOL
cloxiquine
DERMOFONGIN
5-Chloro-8-oxyquinoline
5-chloro-8-quinolino
5-Chloro-8-quinolol
8-Hydroxy-5-chloroquinoline
Chlorisept
Chloroxyquinoline
Cloxyqui
Cloxyquin
Dermofungin
Monochlorohydroxyquinoline
5-CHLORO-8-HYDROXYQUINOLINE CRYSTALLINE
8-Quinolinol, 5-chloro-
Cloxyquine
5-CHLORO-8-QUINOLINOL 99+% | [EINECS(EC#)]
204-978-1 | [Molecular Formula]
C9H6ClNO | [MDL Number]
MFCD00006788 | [Molecular Weight]
179.6 | [MOL File]
130-16-5.mol |
| Chemical Properties | Back Directory | [Appearance]
light green to grey powder | [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]
130-16-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
VC4590000
| [TSCA ]
Yes | [HS Code ]
29334990 |
| Hazard Information | Back Directory | [Chemical Properties]
light green to grey powder | [Uses]
antibacterial, antifungal | [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 |
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