Clioquinol supplier | CasNO.130-26-7

Name
Clioquinol
EINECS 204-984-4
CAS No. 130-26-7
Article Data18
CAS DataBase
Density 2.047 g/cm³
Solubility water: <0.1 g/100 mL at 20 °C
Melting Point 175-183 °C
Formula C₉H₅ClINO
Boiling Point 350.424 °C at 760 mmHg
Molecular Weight 305.502
Flash Point 165.731 °C
Transport Information UN 2811 6.1/PG 3
Appearance Cream-colored to brownish-yellow powder
Safety 36/37/39-45
Risk Codes 25
Molecular Structure
Hazard Symbols T
Synonyms Barquinol;Chinoform;Chloroiodoquine;Cifoform;Dioquinol;Eczecidin;Enteroquinol;Enterozol;Iodochlorhydroxyquin;Iodochloroquine;Iodochloroxyquinoline;Iodoxyquinoline;NSC 3531;Nioform;Quinambicide;Quiniodochlor;Quinoform;Rheaform;Rheaform Boluses;Vioform;5-Chloro-7-iodo-8-oxyquinoline;5-Chloro-7-iodo-8-quinolinol;7-Iodo-5-chloro-8-hydroxyquinoline;8-Hydroxy-7-iodo-5-chloroquinoline;Amebil;Bactol;Clioquinol;
PSA 33.12000
LogP 3.19840

Synthetic route

: 130-16-5
5-Chloro-8-hydroxyquinoline

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

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;

: 7385-89-9
7-iodo-8-hydroxyquinoline

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

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

: 148-24-3
8-quinolinol

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

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;

: 220819-20-5
1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate

A: 130-26-7
5-chloro-7-iodoquinolin-8-ol

B: 110-15-6
succinic acid

C: 443-48-1
metronidazole

D: 13182-87-1
4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]-4-oxobutanoic acid

Conditions

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

...Expand

: 220819-25-0
1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate

A: 130-26-7
5-chloro-7-iodoquinolin-8-ol

B: 88-99-3
benzene-1,2-dicarboxylic acid

C: 443-48-1
metronidazole

D: 126613-32-9
1,2-benzenedicarboxylic acid, mono[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]ester

Conditions

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

...Expand

5-chloro-quinolin-8-ol-iodo chloride-hydrochloride: 5-chloro-quinolin-8-ol-iodo chloride-hydrochloride

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

Conditions	Yield
With water

alkali salt of 5-chloro-8-oxy-quinoline: alkali salt of 5-chloro-8-oxy-quinoline

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

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

: 7647-01-0
hydrogenchloride

: 148-24-3
8-quinolinol

: 7732-18-5
water

iodine trichloride: iodine trichloride

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

Conditions	Yield
anschl. Behandeln mit Wasser;

...Expand

: 27037-46-3
5-chloro-7-iodoquinolin-8-yl ethanoate

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

Conditions	Yield
With sodium hydroxide Heating;

: 1371439-48-3
5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside

A: 492-61-5
β-D-glucose

B: 130-26-7
5-chloro-7-iodoquinolin-8-ol

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 108-24-7
acetic anhydride

: 27037-46-3
5-chloro-7-iodoquinolin-8-yl ethanoate

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 130-16-5
5-Chloro-8-hydroxyquinoline

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: C27H12Cl3GaI3N3O3

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 106-93-4
ethylene dibromide

: 1220348-92-4
C11H7ClINO2

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 109-64-8
1,3-dibromo-propane

: 1220348-94-6
C12H9ClINO2

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 91-13-4
α,α'-dibromo-o-xylene

: 1187578-30-8
C17H11ClINO2

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: C19H19Cl2INORu(1+)*Cl(1-)

Conditions

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

: 1945-84-2
2-ethynylpyridine

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 1218818-91-7
5-chloro-2-(pyridin-2-yl)furo[3,2-h]quinoline

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 205040-71-7
8-((tert-butyldimethylsilyl)oxy)-5-chloro-7-iodoquinoline

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 75-26-3
isopropyl bromide

: 106920-05-2
chloro-5 iodo-7 isopropoxy-8 quinoleine

Conditions

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;

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 1182708-32-2
C19H11ClIN3O2

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 766-83-6
m-chlorophenylacetylene

: 1218818-88-2
5-chloro-2-(3-chlorophenyl)furo[3,2-h]quinoline

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 937-31-5
(4-Nitrophenyl)acetylene

: 1445515-53-6
5-chloro-2-(4-nitrophenyl)furo[3,2-h]quinoline

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 766-49-4
(2-fluorophenyl)acetylene

: 1218818-90-6
5-chloro-2-(2-fluorophenyl)furo[3,2-h]quinoline

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 536-74-3
phenylacetylene

: 1218818-87-1
5-chloro-2-phenylfuro[3,2-h]quinoline

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 3298-98-4
2,3-Bis(bromomethyl)-6,7-dimethylquinoxaline

: 1182708-28-6
C21H15ClIN3O2

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 106-93-4
ethylene dibromide

: 1231156-94-7
7-chloro-9-iodo-2,3-dihydro-1oxa-3a-azoniaphenalene bromide

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 79887-10-8
1-ethynyl-4-(n-pentyl)benzene

: 1445515-43-4
5-chloro-2-(4-phenoxyphenyl)furo[3,2-h]quinoline

Conditions

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%

: 67-56-1
methanol

: 3153-26-2
bis(acetylacetonate)oxovanadium

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: C19H11Cl2I2N2O4V

Conditions

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

...Expand

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: 1258528-67-4
chlorido(5-chloro-7-iodo-8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II)

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 768-60-5
4-methoxyphenylacetylen

: 113503-81-4
5-chloro-2-p-methoxyphenylfuro<3,2-h>quinoline

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: iodido(5-chloro-7-iodo-8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II)

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 98-60-2
4-chlorobenzenesulfonyl chloride

: 4-chloro-benzenesulfonic acid 5-chloro-7-iodo-quinolin-8-yl ester

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 5-chloro-7-iodo-1,2,3,4-tetrahydroquinolin-8-ol

Conditions

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

: 110-52-1
1,4-dibromo-butane

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 1231156-98-1
3-chloro-1-iodo-7,8,9,10-tetrahydro-11-oxa-6a-azoniacycloocta[de]naphthalene bromide

Conditions

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

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 38998-33-3
2,3-di(bromomethyl)naphthalene

: 1260252-51-4
4-chloro-6-iodo-8,15-dihydronaphtho[2',3':6,7][1,4]oxazocino[2,3,4-ij]quinolin-1-one

Conditions

Conditions	Yield
With tetrabutylammomium bromide for 10h;	87%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 4200-06-0
1-(4-ethynylphenoxy)benzene

: 1445515-39-8
5-chloro-2-(4-phenoxyphenyl)furo[3,2-h]quinoline

Conditions

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%

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: 98-59-9
p-toluenesulfonyl chloride

: 63361-49-9
5-chloro-7-iodoquinolin-8-yl 4-methylbenzenesulfonate

Conditions

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

: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

: 130-26-7
5-chloro-7-iodoquinolin-8-ol

: chlorido(5-chloro-7-iodo-8-quinolinolato-k2N,O)(η5-pentamethylcyclopentadienyl)rhodium(III)

Conditions

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

Clioquinol Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Clioquinol Specification

Clioquinol is an antifungal drug and antiprotozoal drug. With the CAS NO.130-26-7, Clioquinol is a quinoline compound that has antibacterial and antifungal properties. It is found in topical preparations to treat skin infections such as infected eczema, athlete's foot and other fungal infections. It is also found in combination preparations with hydrocortisone. It can be found in eye and ear preparations. Clioquinol is mainly used for intestinal amoebic dysentery and bacillary dysentery,and diarrhea caused by taking antibiotics, diarrhea and other nerve.

Physical properties about Clioquinol are: (1)ACD/LogP: 4.171; (2)ACD/LogD (pH 5.5: 3.10; (3)ACD/LogD (pH 7.4): 2.47; (4)ACD/BCF (pH 5.5): 73.89; (5)ACD/BCF (pH 7.4): 17.47; (6)ACD/KOC (pH 5.5): 375.51; (7)ACD/KOC (pH 7.4): 88.78; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.768; (12)Molar Refractivity: 61.87 cm³; (13)Molar Volume: 149.226 cm³; (14)Polarizability: 24.527 10-24cm³; (15)Surface Tension: 70.0690002441406 dyne/cm; (16)Density: 2.047 g/cm³; (17)Flash Point: 165.731 °C; (18)Enthalpy of Vaporization: 61.852 kJ/mol; (19)Boiling Point: 350.424 °C at 760 mmHg

When you are using this chemical, please be cautious about it as the following:
1. Wear suitable protective clothing, gloves and eye/face protection
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H;
(2)InChIKey=QCDFBFJGMNKBDO-UHFFFAOYSA-N;
(3)Smilesc12c(c(cc(c1O)I)Cl)cccn2

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD50	oral	400mg/kg (400mg/kg)	LIVER: OTHER CHANGES	American Journal of Tropical Medicine. Vol. 24, Pg. 29, 1944.
chicken	LDLo	oral	5gm/kg (5000mg/kg)		Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
dog	LD	oral	> 1gm/kg (1000mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1566, 1973
guinea pig	LDLo	oral	175mg/kg (175mg/kg)	LIVER: OTHER CHANGES	American Journal of Tropical Medicine. Vol. 24, Pg. 29, 1944.
guinea pig	LDLo	subcutaneous	200mg/kg (200mg/kg)	BEHAVIORAL: ATAXIA	Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
human	TDLo	oral	1400mg/kg/20D (1400mg/kg)	BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS	Japanese Journal of Medical Science and Biology. Vol. 24, Pg. 195, 1971.
mouse	LD50	intraperitoneal	590mg/kg (590mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
mouse	LD50	oral	69mg/kg (69mg/kg)		Archives of Toxicology, Supplement. Vol. 2, Pg. 371, 1979.
mouse	LD50	subcutaneous	5gm/kg (5000mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
rabbit	LDLo	oral	250mg/kg (250mg/kg)	LIVER: FATTY LIVER DEGERATION LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	JAMA, Journal of the American Medical Association. Vol. 100, Pg. 1658, 1933.
rat	LD50	intraperitoneal	3400mg/kg (3400mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
rat	LD50	subcutaneous	> 5gm/kg (5000mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
women	TDLo	oral	11gm/kg/36W (11000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE	Lancet. Vol. 1, Pg. 1015, 1972.

Product Name

Clioquinol

Synthetic route

Clioquinol Consensus Reports

Clioquinol Specification

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