5,7-Diiodo-8-quinolinol CAS 83-73-8
Introduction：Basic information about 5,7-Diiodo-8-quinolinol CAS 83-73-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
5,7-Diiodo-8-quinolinol Basic information
| Product Name: | 5,7-Diiodo-8-quinolinol |
| Synonyms: | Diiodoquine;Iodoquinol USP;DI-IODOHYDROXYQUINOLINE (IODOQUINOL);10doquinol;Diiodo-oxyquinoline;Diiodoquin;Dijodoxichinoline;Dinoleine |
| CAS: | 83-73-8 |
| MF: | C9H5I2NO |
| MW: | 396.95 |
| EINECS: | 201-497-9 |
| Product Categories: | IOQUIN;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Quinolines, Quinazolines and derivatives;Haloquinolines;Hydroxyquinolines;Quinolines |
| Mol File: | 83-73-8.mol |
5,7-Diiodo-8-quinolinol Chemical Properties
| Melting point | >200 °C (dec.) (lit.) |
| Boiling point | 370.95°C (rough estimate) |
| density | 2.3013 (estimate) |
| storage temp. | Refrigerator |
| solubility | DMSO (Slightly, Heated), Ethyl Acetate (Slightly, Heated) |
| pka | pKa 8.0 (Uncertain) |
| form | Solid |
| color | Pale Yellow to Light Beige |
| Water Solubility | 1g/L at 26℃ |
| Merck | 14,5042 |
| Major Application | pharmaceutical (small molecule) |
| InChI | 1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
| InChIKey | UXZFQZANDVDGMM-UHFFFAOYSA-N |
| SMILES | Oc1c(I)cc(I)c2cccnc12 |
| LogP | 0.602 at 26℃ |
| CAS DataBase Reference | 83-73-8(CAS DataBase Reference) |
| NIST Chemistry Reference | 5,7-Diiodo-8-hydroxyquinoline(83-73-8) |
| EPA Substance Registry System | 5,7-Diiodo-8-quinolinol (83-73-8) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-41 |
| Safety Statements | 26-36/37/39 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| RTECS | VC5775000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29334900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Dam. 1 |
| Hazardous Substances Data | 83-73-8(Hazardous Substances Data) |
| Toxicity | LD50 intravenous in mouse: 56mg/kg |
| Originator | Diiodohydroxyquinoline,Adco Co. |
| Uses | Iodoquinol is an amebocide used against E. histolytica, and it is active against both cysts and trophozoites that are localized in the lumen of the intestine. It is considered the drug of choice for treating asymptomatic or moderate forms of amebiasis. The mechanism of action is unknown. Iodoquinol is used for diseases caused by moderate intestinal amebiasis. Synonyms of this drug are diquinol, iodoxin, diiodoquin, amebaquin, and others. |
| Uses | It acts as an amoebicidal and so used in the treatment of amoebiasis, balantidiasis (an infection caused by protozoa). |
| Indications | Iodoquinol (diiodohydroxyquin, Yodoxin, Moebiquin)is a halogenated 8-hydroxyquinoline derivative whoseprecise mechanism of action is not known but is thoughtto involve an inactivation of essential parasite enzymes.Iodoquinol kills the trophozoite forms of E. histolytica,B. coli, B. hominis, and Dientamoeba fragilis. Iodoquinol is absorbed from the gastrointestinaltract and is excreted in the urine as glucuronide and sulfateconjugates. Most of an orally administered dose isexcreted in the feces. Iodoquinol has a plasma half-lifeof about 12 hours. Iodoquinol is the drug of choice in the treatment ofasymptomatic amebiasis and D. fragilis infections. It is also used in combination with other drugs in the treatmentof other forms of amebiasis and as an alternativeto tetracycline in the treatment of balantidiasis. Adverse reactions are related to the iodine contentof the drug; the toxicity is often expressed as skin reactions,thyroid enlargement, and interference with thyroidfunction studies. Headache and diarrhea also occur.Chronic use of clioquinol, a closely related agent,has been linked to a myelitislike illness and to optic atrophywith permanent loss of vision. |
| Definition | ChEBI: Iodoquinol is a monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by iodine. It is considered the drug of choice for treating asymptomatic or moderate forms of amoebiasis. It has a role as an antiamoebic agent, an antibacterial agent, an antiseptic drug and an antiprotozoal drug. It is a monohydroxyquinoline and an organoiodine compound. |
| Manufacturing Process | 5,7-Diiodo-8-quinolinol widely used as an intestinal antiseptic, especially as anantiamebic agent. It is also used topically in other infections and may causeCNS and eye damage. It is known by very many similar trade namesworldwide. 0.01 mol 8-oxychinoline and 0.01 mol salicylic acid were dissolved in 500 mlof water and then 0.05 mol potassium iodide was added. The mixture washeated to temperature 90°-100°C. After that 0.01 mol of KIO3 by little tileswas added. The next tile was added after a disappearence of dischargingiodine. Then 10 ml 2 N HCl was added. The solid product was fallen, filteredoff, washed with hot water and in 0.25 N NaOH dissolved. The solution wasfiltered and the clear filtrate precipitated with a very little excess of HCl. Theproduct 5,7-diiodo-8-quinolinol was filtered, washed with hot water and dried.MP: 200°-250°C (with decomposition). |
| Brand name | Quinadome(Bayer); Yodoxin (Glenwood). |
| Therapeutic Function | Antibacterial |
| Flammability and Explosibility | Non flammable |
| Clinical Use | 5,7-Diiodo-8-quinolinol, 5,7-diiodo-8-hydroxyquinoline,or diiodohydroxyquin (Yodoxin, Diodoquin, Diquinol) is ayellowish to tan microcrystalline, light-sensitive substancethat is insoluble in water. It is recommended for acute andchronic intestinal amebiasis but is not effective in extraintestinaldisease. Because a relatively high incidence of topicneuropathy has occurred with its use, iodoquinol should notbe used routinely for traveler’s diarrhea. |
| Safety Profile | Poison by ingestion and intravenous routes. Human systemic effects by ingestion: eye effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Iand Nox |
| Synthesis | Iodoquinol, 5,7-diiodo-8-quinolinol (37.2.2), is made by iodination of 8-oxyquinoline (37.2.1) using a mixture of potassium iodide/potassium iodate. The initial8-hydroxyquinolin (37.2.1) is made from 2-aminophenol and glycerol in the presence ofsulfuric acid and nitrobenzene (Skraup synthesis). |
| Purification Methods | It crystallises from xylene and is dried at 70o in a vacuum. [Beilstein 21 II 58.] |
| References | [1] Tetrahedron, 2008, vol. 64, # 1, p. 234 - 239 [2] Tetrahedron Letters, 2001, vol. 42, # 11, p. 2089 - 2092 [3] Patent: WO2016/113757, 2016, A1. Location in patent: Page/Page column 18-19 [4] Molecules, 2005, vol. 10, # 10, p. 1307 - 1317 [5] Monatshefte fur Chemie, 2012, vol. 143, # 4, p. 619 - 623 |
5,7-Diiodo-8-quinolinol Preparation Products And Raw materials
| Raw materials | 8-Hydroxyquinoline-->Potassium iodate-->Potassium iodide-->Salicylic acid-->1,2-Benzenedicarboxylic acid, 1-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl] ester-->[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl] hydrogen succinate-->Metronidazole-->Water-->Phthalic acid-->Iodine monochloride-->Hydrochloric acid-->Succinic acid |
| Preparation Products | 5-iodo-8-quinolinol-->5,7-Dichloro-8-hydroxyquinoline |
