5-Chloro-8-hydroxyquinoline CAS 130-16-5
5-Chloro-8-hydroxyquinoline Basic information
| Product Name: | 5-Chloro-8-hydroxyquinoline |
| Synonyms: | 5-Chloro-8-quinolinol, >=98%;5-CHLORO-8-HYDROXYQUINOLINE;5-CHLORO-8-QUINOLINOL;5-CHLOROOXINE;5-CHLOROQUINOPHENOL;Clioquinol EP Impurity A;5-Chloro-8-oxyquinoline;5-chloro-8-quinolino |
| CAS: | 130-16-5 |
| MF: | C9H6ClNO |
| MW: | 179.6 |
| EINECS: | 204-978-1 |
| Product Categories: | Quinolines;Haloquinolines;Quinolines, Quinazolines and derivatives;Hydroxyquinolines;pesticide intermediates;API;130-16-5 |
| Mol File: | 130-16-5.mol |
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) |
| pka | 3.77±0.10(Predicted) |
| form | Powder |
| color | Light green to gray |
| Sensitive | Light Sensitive |
| Merck | 14,2422 |
| BRN | 5289 |
| InChI | 1S/C9H6ClNO/c10-7-3-4-8(12)9-6(7)2-1-5-11-9/h1-5,12H |
| InChIKey | RWPWQYXFGFYJBA-UHFFFAOYSA-N |
| SMILES | Oc1ccc(Cl)c2cccnc12 |
| 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 | TSCA listed |
| HS Code | 29334990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 Eye Irrit. 2 Skin Sens. 1 |
| 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 | 3054-95-3 95-85-2 130-16-5 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 Preparation Products And Raw materials
| Raw materials | 8-Hydroxyquinoline-->Acrolein diethyl acetal-->2-Amino-4-chlorophenol-->Water-->Hydrochloric acid |
| Preparation Products | 1,2,3,4-Tetrahydro-8-hydroxyquinoline-->Quinoline, 5-chloro-8-phenoxy--->5-CHLORO-1,2,3,4-TETRAHYDRO-QUINOLIN-8-OL-->8-Quinolinol, 5-chloro-7-(2-propen-1-yl)- |
