130-26-7

Basic information

• Product Name: Clioquinol
• Synonyms: 5-Chlor-7-jod-8-hydroxy-chinolin;5-chloro-7-iodo-8-quinolino;7-Iodo-5-chloroxine;8-Quinolinol, 5-chloro-7-iodo-;ala-quin;Alchloquin;alchoquin;alioform
• CAS NO: 130-26-7
• Molecular Formula: C₉H₅ClINO
• Molecular Weight: 305.5
• EINECS: 204-984-4
• Product Categories: Quinolines, Quinazolines and derivatives;Haloquinolines;Hydroxyquinolines;Quinolines;Miscellaneous Compounds;Pharmaceutical intermediate;Building Blocks;C8 to C10;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 130-26-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 175-183 °C
• Boiling Point: 350.424 °C at 760 mmHg
• Flash Point: 165.731 °C
• Appearance: Cream-colored to brownish-yellow powder
• Density: 1.8959 (estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.753
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (>25 mg/ml), boiling alcohol ((1:43)), methan
• PKA: pKa 8.12(50%aqEtOH t=35.0±0.1 I=0.00 N2atmosphere)(Approximate)
• Water Solubility: <0.1 g/100 mL at 20℃
• Merck: 14,5031
• BRN: 153637
• CAS DataBase Reference: Clioquinol(CAS DataBase Reference)
• NIST Chemistry Reference: Clioquinol(130-26-7)
• EPA Substance Registry System: Clioquinol(130-26-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: VC5075000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 130-26-7(Hazardous Substances Data)

Usage

Chemical Properties

Almost white, light yellow, brownish-yellow or yellowish-grey powder.

Originator

Clioquinol,CIBA-GEIGY Corp.

Uses

Different sources of media describe the Uses of 130-26-7 differently. You can refer to the following data:
1. Clioquinol is used as an anti-infective agent; antiamoebic agent; intravaginal trichomonacide; used to impregnate cotton bandages for antibacterial purposes; in animals as an intestinal anti-infective agent.
2. alpha adrenergic blocker, mydriatic, antidepressant
3. Used as a topical antifungal treatment

Definition

ChEBI: A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has al o been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.

Indications

Iodochlorhydroxyquin (Clioquinol), containing 40% iodine, was originally developed as a substitute for iodoform as an antiseptic dusting powder. Although its most effective use is in the treatment of amebiasis, it also has mild antibacterial and antifungal effects and may be used alone or with steroids in the treatment of eczematous and impetiginized processes and some dermatophyte, yeast, and Trichomonas infections. However, more specific agents are available. Because of neurotoxicity, the oral form of this drug has been withdrawn in the United States. A recent study demonstrating significant percutaneous absorption when applied to intact human skin raises concern regarding its topical use as well. The medication may stain the skin, hair, and clothing yellow and may induce contact allergy.

Manufacturing Process

Chlor-5-oxy-8-chinoline (18 kg) was mixed with potassium hydroxide (6.0 kg), water (400 kg) and heated. To this solution 50 L saturated aqueous solution of potassium iodide (16.6 kg) was added, mixed and continued to heat. Solution was filtered at room temperature. Then to this yellow solution the solution of chloride of lime and 50 kg 5% solution of were added then all this was mixed and allowed to stand for 24 h. After eliminating of free iodine by addition of sodium thiosulfate the obtained precipitate was washed with water. To residue 1% solution of acidum hydrochloricum (50.0 kg) and rapidly was heated to 50°C. Then it was washed with water and dried, so 5-chloro-7-iodo-quinolinol-8 was obtained, melting point 170°-175°C.

Brand name

Domeform-HC (Bayer); Quin-O-Creme (Marion Merrell Dow); Rheaform Boluses [Veterinary] (Fort Dodge Animal Health); Vioform (Ciba-Geigy);Amebio-formo;Anterobe;Aristoform "d";Aristoform "r";Barquinol hc;Betnorate-c;Britaderm;Britadex-vioform;Carboform;Cloro-yodo-hidroxi;Clorpine;Combias;Copover;Cortex;Corti-glottyl;Dependal;Dermo-quinol;Dermozolan;Dexalocal;Diaban;Dioderm c-c;Diodotracin;Dizenterol;Enteral;Ente-rivo;Enterokin;Enterosan;Entero-valodon;Entero-vioformo;Enterquinol;Entox;Entrasorb;Entrokinol;Fusalor-yodocloro;Fyloxxal;Gmd;Guanosept;Haelan-c;Hocacorten-vioform;Hydroform;Iodo-cortifair;Iodocortindon;Iodo-max;Isoderm;Khlorlinkotsin;Klinicin;Lecortin;Lederform-d;Lemoderm;Linola;Locorten-vioform;Metrijet;Metrityl;Mexafermento;Mexafom;Nasello;Nefurox;Obstecrim;Pedi-cort;Percural;Phen-ortis;Pricort cream;Propaderm-c;Quadriderm;Quin iii;Quina band;Quiniodochlor;Reticus;Sebryl;Sedacol;Septo-canulase;Silic c;Tequinophil;Toptic;Torofor;Unidiarea;Uteroject;Ventribex;Viform;Vioform bolus;Vioform hydrocortisan;Vioform hydrocortisone;Vioforme.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Clioquinol, a halogenated hydroxyquinoline derivative, was introduced into medicine around 1900 as a topical antiseptic and in 1934 oral preparations for the treatment of amoebic dysentery and simple diarrhoea became available. By 1964 its use in Japan had been associated with cases of sub-acute myelo-optic neuropathy (SMON) which reached epidemic proportions resulting in its withdrawal there in 1970. Although relatively few cases of SMON were documented elsewhere, clioquinol was subsequently withdrawn from use in many countries and placed under prescription control in others. It was phased out worldwide by the major manufacturer between 1983 and 1985 on grounds of obsolescence. No adequately controlled evidence was ever generated to demonstrate that clioquinol is effective in bacterial or viral diarrhoea. However, products containing clioquinol and related halogenated hydroxyquinolines continue to be used in some tropical and subtropical countries where amoebiasis remains endemic. Other amoebocides are preferred in the WHO Model List of Essential Drugs. (Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)

General Description

Cream-colored to brownish-yellow powder. Practically odorless. Decomposes at 178-179°C. Used as a topical anti-infective.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Clioquinol is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides . Darkens on exposure to light.

Fire Hazard

Flash point data for Clioquinol are not available; however, Clioquinol is probably combustible.

Flammability and Explosibility

Nonflammable

Clinical Use

5-Chloro-7-iodo-8-quinolinol, 5-chloro8-hydroxy-7-iodoquinoline, or iodochlorhydroxyquin (Vioform) occursas a spongy, light-sensitive, yellowish white powder that isinsoluble in water. Vioform was initially used as a substitutefor iodoform in the belief that it released iodine in the tissues.It has been used as a powder for many skin conditions,such as atopic dermatitis, eczema, psoriasis, and impetigo.A 3% ointment or cream has been used vaginally as a treatmentfor Trichomonas vaginalis vaginitis. The best use forVioform is in the topical treatment of fungal infections suchas athlete’s foot and jock itch. A combination with hydrocortisone(Vioform HC) is also available.

Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: change in central nervous system electrical function, optic nerve damage, and changes in vision. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, I-, and NOx.

Purification Methods

It crystallises from AcOH or xylene and dry it at 70o in vacuo.[Beilstein 21 III/IV 1190.]

InChI:InChI=1/C10H6ClIO/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,13H

Synthetic route

5-Chloro-8-hydroxyquinoline (130-16-5) → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With 1-butyl-3-methyl-pyridinium dichloroiodate at 80℃; for 1h; Inert atmosphere;	94%
Stage #1: With iodine; tert-butylamine In chloroform; toluene at -78℃; Stage #2: 5-Chloro-8-hydroxyquinoline In chloroform; toluene at -78 - 20℃; for 0.75h;

7-iodo-8-hydroxyquinoline (7385-89-9) → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With trichloroisocyanuric acid In acetonitrile at 20℃; for 2h;	65%

8-quinolinol (148-24-3) → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With tetrachloromethane; iodine trichloride Behandeln des Reaktionsprodukts mit Wasser;
With iodine trichloride; acetic acid Behandeln des jeweils erhalten Reaktionsprodukts mit Wasser;
With hydrogenchloride; iodine trichloride Behandeln des jeweils erhalten Reaktionsprodukts mit Wasser;

1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate (220819-20-5) → 5-chloro-7-iodoquinolin-8-ol (130-26-7) + succinic acid (110-15-6) + metronidazole (443-48-1) + 4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]-4-oxobutanoic acid (13182-87-1)

Conditions	Yield
With phosphate buffer; potassium chloride In methanol at 37℃; Rate constant; var. pH; also with human plasma and rat liver homogenate;

1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate (220819-25-0) → 5-chloro-7-iodoquinolin-8-ol (130-26-7) + benzene-1,2-dicarboxylic acid (88-99-3) + metronidazole (443-48-1) + 1,2-benzenedicarboxylic acid, mono[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]ester (126613-32-9)

Conditions	Yield
With phosphate buffer; potassium chloride In methanol at 37℃; Rate constant; var. pH; also with human plasma and rat liver homogenate;

5-chloro-quinolin-8-ol-iodo chloride-hydrochloride → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With water

alkali salt of 5-chloro-8-oxy-quinoline → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With water; iodine; potassium iodide
With sodium hypochlorite; water; potassium iodide

hydrogenchloride (7647-01-0) + 8-quinolinol (148-24-3) + water (7732-18-5) + iodine trichloride → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
anschl. Behandeln mit Wasser;

5-chloro-7-iodoquinolin-8-yl ethanoate (27037-46-3) → 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With sodium hydroxide Heating;

5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside (1371439-48-3) → β-D-glucose (492-61-5) + 5-chloro-7-iodoquinolin-8-ol (130-26-7)

Conditions	Yield
With β-glucosidase from almonds; water at 37℃; for 4h; pH=7; Reagent/catalyst; Enzymatic reaction;

5-chloro-7-iodoquinolin-8-ol (130-26-7) + acetic anhydride (108-24-7) → 5-chloro-7-iodoquinolin-8-yl ethanoate (27037-46-3)

Conditions	Yield
With pyridine at 60℃; for 0.0833333h;	100%
at 150℃; for 5h;	94%
With pyridine

5-chloro-7-iodoquinolin-8-ol (130-26-7) → 5-Chloro-8-hydroxyquinoline (130-16-5)

Conditions	Yield
With piperidine; palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 24h; Autoclave;	100%
With pyridine for 4h; Heating;	94%

gallium(III) trichloride + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → C27H12Cl3GaI3N3O3

Conditions	Yield
With sodium acetate In ethanol; water for 3h; pH=5 - 6; Reflux;	98%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + ethylene dibromide (106-93-4) → C11H7ClINO2 (1220348-92-4)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	95%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 1,3-dibromo-propane (109-64-8) → C12H9ClINO2 (1220348-94-6)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	95%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + α,α'-dibromo-o-xylene (91-13-4) → C17H11ClINO2 (1187578-30-8)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	95%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) → C19H19Cl2INORu(1+)*Cl(1-)

Conditions	Yield
In methanol at 20℃; for 0.5h;	95%

2-ethynylpyridine (1945-84-2) + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → 5-chloro-2-(pyridin-2-yl)furo[3,2-h]quinoline (1218818-91-7)

Conditions	Yield
With aluminum oxide; copper(l) iodide In chloroform at 130℃; for 0.1h; Sonogashira cross-coupling reaction; Microwave irradiation;	94%
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	83%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 8-((tert-butyldimethylsilyl)oxy)-5-chloro-7-iodoquinoline (205040-71-7)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 12h; Inert atmosphere;	94%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + isopropyl bromide (75-26-3) → chloro-5 iodo-7 isopropoxy-8 quinoleine (106920-05-2)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 16h;	93%
	91%
With potassium carbonate In dimethyl sulfoxide at 20℃;	55%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;

2,3-bis(bromomethyl)quinoxaline (3138-86-1) + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → C19H11ClIN3O2 (1182708-32-2)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 10h;	92%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + m-chlorophenylacetylene (766-83-6) → 5-chloro-2-(3-chlorophenyl)furo[3,2-h]quinoline (1218818-88-2)

Conditions	Yield
With aluminum oxide; copper(l) iodide In chloroform at 130℃; for 0.1h; Sonogashira cross-coupling reaction; Microwave irradiation;	92%
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	88%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + (4-Nitrophenyl)acetylene (937-31-5) → 5-chloro-2-(4-nitrophenyl)furo[3,2-h]quinoline (1445515-53-6)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	92%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + (2-fluorophenyl)acetylene (766-49-4) → 5-chloro-2-(2-fluorophenyl)furo[3,2-h]quinoline (1218818-90-6)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	91%
With aluminum oxide; copper(l) iodide In chloroform at 130℃; for 0.1h; Sonogashira cross-coupling reaction; Microwave irradiation;	88%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + phenylacetylene (536-74-3) → 5-chloro-2-phenylfuro[3,2-h]quinoline (1218818-87-1)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine In water at 80℃; for 1h; Reagent/catalyst; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	91%
With aluminum oxide; copper(l) iodide In chloroform at 130℃; for 0.1h; Sonogashira cross-coupling reaction; Microwave irradiation;	90%
Stage #1: 5-chloro-7-iodoquinolin-8-ol With copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 0.5h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: phenylacetylene In N,N-dimethyl-formamide at 80℃; for 48h; Sonogashira Cross-Coupling; Inert atmosphere;	75%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 2,3-Bis(bromomethyl)-6,7-dimethylquinoxaline (3298-98-4) → C21H15ClIN3O2 (1182708-28-6)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 16h;	90%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + ethylene dibromide (106-93-4) → 7-chloro-9-iodo-2,3-dihydro-1oxa-3a-azoniaphenalene bromide (1231156-94-7)

Conditions	Yield
With Amberlite IRA 402(OH) resin In water at 80℃; for 3h; Inert atmosphere;	90%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 1-ethynyl-4-(n-pentyl)benzene (79887-10-8) → 5-chloro-2-(4-phenoxyphenyl)furo[3,2-h]quinoline (1445515-43-4)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	90%

methanol (67-56-1) + bis(acetylacetonate)oxovanadium (3153-26-2) + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → C19H11Cl2I2N2O4V

Conditions	Yield
With acetic acid for 2h; Reflux;	90%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) → chlorido(5-chloro-7-iodo-8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II) (1258528-67-4)

Conditions	Yield
In methanol; dichloromethane at 65℃; for 6h; Reflux;	89.6%
With sodium methylate In methanol Reflux; Inert atmosphere; Schlenk technique;	73%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 4-methoxyphenylacetylen (768-60-5) → 5-chloro-2-p-methoxyphenylfuro<3,2-h>quinoline (113503-81-4)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	89%

diiodo(p-cymene)ruthenium(II) dimer + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → iodido(5-chloro-7-iodo-8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II)

Conditions	Yield
In methanol; dichloromethane at 65℃; for 6h; Reflux;	88.9%
With sodium methylate In methanol; chloroform at 20℃; for 1h; Inert atmosphere; Schlenk technique;	65%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 4-chloro-benzenesulfonic acid 5-chloro-7-iodo-quinolin-8-yl ester

Conditions	Yield
With pyridine at 20℃; Inert atmosphere;	88%

5-chloro-7-iodoquinolin-8-ol (130-26-7) → 5-chloro-7-iodo-1,2,3,4-tetrahydroquinolin-8-ol

Conditions	Yield
With hydrogen; dihydrogen hexachloroplatinate In water; isopropyl alcohol at 90 - 95℃; under 15001.2 Torr;	87%

1,4-dibromo-butane (110-52-1) + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → 3-chloro-1-iodo-7,8,9,10-tetrahydro-11-oxa-6a-azoniacycloocta[de]naphthalene bromide (1231156-98-1)

Conditions	Yield
With Amberlite IRA 402(OH) resin In water at 80℃; for 4h; Inert atmosphere;	87%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 2,3-di(bromomethyl)naphthalene (38998-33-3) → 4-chloro-6-iodo-8,15-dihydronaphtho[2',3':6,7][1,4]oxazocino[2,3,4-ij]quinolin-1-one (1260252-51-4)

Conditions	Yield
With tetrabutylammomium bromide for 10h;	87%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + 1-(4-ethynylphenoxy)benzene (4200-06-0) → 5-chloro-2-(4-phenoxyphenyl)furo[3,2-h]quinoline (1445515-39-8)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine at 80℃; for 1h; Sonogashira Cross-Coupling; Green chemistry; regioselective reaction;	87%

5-chloro-7-iodoquinolin-8-ol (130-26-7) + p-toluenesulfonyl chloride (98-59-9) → 5-chloro-7-iodoquinolin-8-yl 4-methylbenzenesulfonate (63361-49-9)

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; for 3h;	87%

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer + 5-chloro-7-iodoquinolin-8-ol (130-26-7) → chlorido(5-chloro-7-iodo-8-quinolinolato-k2N,O)(η5-pentamethylcyclopentadienyl)rhodium(III)

Conditions	Yield
In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; Darkness;	87%

Upstream product

• 27037-46-3 5-chloro-7-iodoquinolin-8-yl ethanoate 
• 7385-89-9 8-hydroxy-7-iodoquinoline 
• 2598-29-0 8-acetyloxyquinoline 
• 10173-02-1 5-chloroquinoline-8-yl acetate 
• 1371439-48-3 5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside 
• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 7647-01-0 hydrogenchloride 
• 148-24-3 8-quinolinol 
• 7732-18-5 water 
• 220819-25-0 1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate 
• 220819-20-5 1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate 

Downstream Products

• 773-76-2 chloroxine 
• 83-73-8 5,7-diiodo-8-hydroxyquinoline 
• 205040-71-7 8-((tert-butyldimethylsilyl)oxy)-5-chloro-7-iodoquinoline 
• 205038-08-0 5-Chloro-7-(Dimethylphenylsilyl)-8-Quinolinol 
• 15731-41-6 Cu(5-chloro-7-iodo-8-hydroxyquinoline(1-))2 
• 15731-41-6 [Cu(CQ)₂] 
• 63361-49-9 5-chloro-7-iodoquinolin-8-yl 4-methylbenzenesulfonate 
• 1218818-87-1 5-chloro-2-phenylfuro[3,2-h]quinoline 
• 1218818-90-6 5-chloro-2-(2-fluorophenyl)furo[3,2-h]quinoline 

Related news

In‐vitro antimicrobial, thermal and spectral studies of mixed ligand Cu(II) heterochelates of Clioquinol (cas 130-26-7) and coumarin derivatives09/26/2019

The mixed‐ligand heterochelates of Cu(II) with 5‐chloro‐7‐iodo‐8‐hydroxyquinoline (clioquinol) and various uninegative bidentate ligands were prepared. The structure of mixed‐ligand heterochelates was investigated using spectral, physicochemical, elemental analysis and thermal studies. Th...detailed

Relevant articles and documents

-

-

One-pot method for preparing chloroquine chloroquine and diiodoquinoline

The method effectively solves the problems of (1) solving the problem of high isomer ratio in reaction products due to the fact that hydroxyl groups are ortho-alignment positioning groups when no guide groups are first C5 halogenated and C7 iodo, and purification difficulty is also increased. (2) The problems of poor atom economy, harsh reaction conditions, tedious aftertreatment steps and the like in first 66% steps C5 C7 C7 are effectively overcome by the method provided by the invention, and the C5-position halogenated product is 60% effectively overcome by overcoming the defects of poor atom economy, harsh reaction conditions, complicated post-treatment steps and the like in the two methods. The method has the advantages of economy of atoms, simplicity in operation, easiness in amplification and the like.

NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS

The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).

Nonreductive deiodination of ortho-iodo-hydroxylated arenes using tertiary amines

A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes inch ding derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.