5-Chloro-8-hydroxyquinoline supplier

Name
5-Chloro-8-hydroxyquinoline
EINECS 204-978-1
CAS No. 130-16-5
Article Data31
CAS DataBase
Density 1.412 g/cm³
Solubility
Melting Point 122-124 °C(lit.)
Formula C₉H₆ClNO
Boiling Point 348.7 °C at 760 mmHg
Molecular Weight 179.606
Flash Point 164.7 °C
Transport Information
Appearance light green to grey powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Cloxiquine;Cloxyquin;Dermofongin;Dermofungin;NSC 35083;NSC 53182;NSC 74943;5-Chloro-8-hydroxy quinoline;5-Chloro-8-oxyquinoline;5-Chloro-8-quinolinol;5-Chloro-quinoline-8-ol;5-Chlorooxine;8-Hydroxy-5-chloroquinoline;8-Quinolinol,5-chloro-;
PSA 33.12000
LogP 2.59380

Synthetic route

: 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%

: 1198-14-7
5-bromo-8-hydroxyquinoline

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

Conditions

Conditions	Yield
With pyridine hydrochloride at 220℃; for 0.166667h;	93%

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

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

Conditions

Conditions	Yield
With pyridine; water Heating;	92%
Multi-step reaction with 2 steps 1: NaOH / Heating 2: 94 percent / pyridine / 4 h / Heating View Scheme

: 148-24-3
8-quinolinol

A: 773-76-2
chloroxine

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

Conditions

Conditions	Yield
With trichloroisocyanuric acid In acetonitrile at 20℃; regioselective reaction;	A 13% B 71%
With sulfuryl dichloride; chloroform

: 3054-95-3
acrylaldehyde diethyl acetal

: 95-85-2
2-hydroxy-5-chloro-aniline

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

Conditions

Conditions	Yield
With hydrogenchloride In water at 111℃; for 24h; Doebner-von Miller Reaction;	49%

: 148-24-3
8-quinolinol

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

Conditions

Conditions	Yield
With hydrogenchloride; iron(III) chloride
With hydrogenchloride; water anschliessendes Behandeln mit Chlor.;

: 16862-11-6
8-Hydroxyquinoline hydrochloride

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

Conditions

Conditions	Yield
With sulfuryl dichloride; chloroform

: 89-64-5
p-chloro-o-nitrophenol

: 56-81-5
glycerol

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

Conditions

Conditions	Yield
With formic acid; sulfuric acid
With sulfuric acid; acetic acid
With phosphoric acid; sulfuric acid

: 56-81-5
glycerol

: 95-85-2
2-hydroxy-5-chloro-aniline

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

Conditions

Conditions	Yield
With arsenic(V) oxide; sulfuric acid at 150 - 160℃;
With sulfuric acid at 90℃; for 0.25h;

: 56-81-5
glycerol

: 88-75-5
2-hydroxynitrobenzene

A: 148-24-3
8-quinolinol

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

Conditions

Conditions	Yield
With hydrogenchloride; water at 175℃;

...Expand

: 10140-89-3
2,3-dichloropropanal

: 95-85-2
2-hydroxy-5-chloro-aniline

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

Conditions

Conditions	Yield
With phosphoric acid; water at 135℃;

: 89-64-5
p-chloro-o-nitrophenol

: 95-85-2
2-hydroxy-5-chloro-aniline

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

Conditions

Conditions	Yield
With sulfuric acid; glycerol

5-bromo-8-oxy-quinoline: 5-bromo-8-oxy-quinoline

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

Conditions

Conditions	Yield
With hydrogenchloride at 160 - 170℃;

8-oxy-quinoline-sulfonic acid-(5): 8-oxy-quinoline-sulfonic acid-(5)

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

Conditions

Conditions	Yield
With phosphorus pentachloride at 170℃;

: 148-24-3
8-quinolinol

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

B 5.7-dichloro-8-oxy-quinoline: 5.7-dichloro-8-oxy-quinoline

Conditions

Conditions	Yield
With chlorine; acetic acid

: 773-76-2
chloroxine

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

A: 492-61-5
β-D-glucose

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; tetrabutylammomium bromide / methanol; water; dichloromethane / 68 h / 20 °C 2: β-glucosidase from almonds; water / aq. phosphate buffer / 0.67 h / 37 °C / pH 7.4 / Enzymatic reaction View Scheme

...Expand

: 1419402-06-4
5,7-dichloro-8-quinolinyl-β-D-glucopyranoside

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: β-glucosidase from almonds; water / aq. phosphate buffer / 0.67 h / 37 °C / pH 7.4 / Enzymatic reaction 2: potassium carbonate; tetrabutylammomium bromide / methanol; water; dichloromethane / 68 h / 20 °C 3: β-glucosidase from almonds; water / aq. phosphate buffer / 0.67 h / 37 °C / pH 7.4 / Enzymatic reaction View Scheme

: 101111-68-6
5-chloro-8-quinolinyl-β-D-glucopyranoside

A: 492-61-5
β-D-glucose

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

Conditions

Conditions	Yield
With β-glucosidase from almonds; water In aq. phosphate buffer at 37℃; for 0.666667h; pH=7.4; Reagent/catalyst; Enzymatic reaction;

: 107-02-8
acrolein

: 95-85-2
2-hydroxy-5-chloro-aniline

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

Conditions

Conditions	Yield
With hydrogenchloride; p-chloro-o-nitrophenol; acetic acid In water for 6h; Reflux; Large scale;

: 55-21-0
benzamide

: 1122-91-4
4-bromo-benzaldehyde

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

: N-((4-bromophenyl)(5-chloro-8-hydroxyquinolin-7-yl)methyl)benzamide

Conditions

Conditions	Yield
at 130 - 180℃; for 3h; Betti Reaction;	100%

...Expand

: 1633-84-7
4-chloro-1-butanesulfonyl chloride

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

: C13H13Cl2NO3S

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 5h;	100%

: 50-00-0
formaldehyd

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

: 23978-55-4
1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

: 7,16-bis(5-chloro-8-hydroxyquinoline-7-ylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

Conditions

Conditions	Yield
In 1,4-dioxane for 2h; Mannich reaction; Inert atmosphere; Microwave irradiation;	99%
In toluene for 2h; Product distribution / selectivity; Microwave irradiation;	99%
In toluene for 20h; Condensation; Mannich reaction; Heating;	68%

...Expand

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

: 98-59-9
p-toluenesulfonyl chloride

: 1108187-77-4
5-chloroquinolin-8-yl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
Stage #1: 5-Chloro-8-hydroxyquinoline With sodium hydroxide In water for 0.5h; Reflux; Stage #2: p-toluenesulfonyl chloride In water; acetone at 20℃;	99%
With copper(l) iodide; caesium carbonate In water; acetone at 20℃; for 0.666667h;	93.4%
With sodium hydroxide In water; acetone at 20℃; for 3h;	83%

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

: 77-78-1
dimethyl sulfate

: 17012-44-1
chloro-5 methoxy-8 quinoleine

Conditions

Conditions	Yield
Stage #1: 5-Chloro-8-hydroxyquinoline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.5h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide; mineral oil for 2.5h;	97%
With potassium hydroxide In water; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	55%
With sodium hydroxide; water

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

: 54810-34-3
5-chloro-8-hydroxy-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With hydrogen In water at 20℃; under 760.051 Torr; for 0.666667h;	97%
With hydrogen In toluene at 80℃; under 15001.5 Torr; for 13h; Autoclave; chemoselective reaction;	88%
Stage #1: 5-Chloro-8-hydroxyquinoline With H2SiEt2; tris(pentafluorophenyl)borate In chloroform at 85℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h;	67%
With sodium tetrahydroborate In water; N,N-dimethyl-formamide at 60℃; under 760.051 Torr; for 8h; Catalytic behavior; Inert atmosphere;

: 870-50-8
di-tert-butyl-diazodicarboxylate

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

: di-tert-butyl 1-(5-chloro-8-hydroxyquinolin-7-yl)hydrazinyl-1,2-dicarboxylate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 6h;	97%

: 110-89-4
piperidine

: 50-00-0
formaldehyd

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

: 5-chloro-7-(piperidin-1-ylmethyl)quinolin-8-ol

Conditions

Conditions	Yield
With triethylamine In ethanol for 12h; Mannich reaction; Reflux;	96%
In ethanol at 80℃; for 24h;	95.1%

...Expand

: 1633-82-5
3-chloro-n-propanesulfonyl chloride

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

: C12H11Cl2NO3S

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1.75h;	96%

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

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

: 1182708-30-0
C19H12ClN3O2

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 12h;	95%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	90%

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

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

: [(η6-pcymene)RuCl(κ2-O,N-5-chloro-(8-hydroxyquinoline))]·Cl

Conditions

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

: 1868-58-2
3-bromo-2-fluoro-5-nitropyridine

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

: 8-((3-bromo-5-nitropyridin-2-yl)oxy)-5-chloroquinoline

Conditions

Conditions	Yield
With potassium phosphate; TPGS-750-M In water at 45℃; for 12h; Inert atmosphere;	95%

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

: 5-chloroquinolin-8-yl sulfurofluoridate

Conditions

Conditions	Yield
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; potassium carbonate In dimethyl sulfoxide at 20℃; for 1h;	95%
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.166667h;	92%
With potassium fluoride; triethylamine; N,N`-sulfuryldiimidazole; trifluoroacetic acid In dichloromethane at 20℃; for 18h;	87%

: 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;

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

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

: 1182708-26-4
C21H16ClN3O2

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	94%
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 14h;	90%

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

: 1029498-94-9
lithium 5-chloro-8-hydroxyquinolate

Conditions

Conditions	Yield
With lithium In acetonitrile for 0.416667h;	94%

: 150602-89-4
1,4-dioxa-7,13-dithia-10-azacyclopentadecane

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

paraformaldehyde: paraformaldehyde

: 1-(5-chloro-8-hydroxy-7-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane

Conditions

Conditions	Yield
In benzene for 48h; Reflux; Inert atmosphere;	94%

...Expand

: 619-21-6
m-formylphenyl benzoic acid

: 55-21-0
benzamide

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

: 3-(benzamido(5-chloro-8-hydroxyquinolin-7-yl)methyl)benzoic acid

Conditions

Conditions	Yield
at 130 - 180℃; for 3h; Betti Reaction;	94%

...Expand

: 5292-43-3
bromoacetic acid tert-butyl ester

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

: tert-butyl 2-((5-chloroquinolin-8-yl)oxy)acetate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 50℃;	94%

: 110-86-1
pyridine

: cobalt(II) nitrate hexahydrate

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

: C28H20Cl2CoN4O2

Conditions

Conditions	Yield
In ethanol at 80℃; for 72h; High pressure;	94%

...Expand

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

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

: 5-chloroquinolin-8-yl 2-nitrobenzenesulfonate

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In water; acetone at 20℃; for 0.666667h;	94%

: 100-39-0
benzyl bromide

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

: 8-(benzyloxy)-5-chloro-quinoline

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In water; acetone at 20℃; for 0.666667h;	94%

: 1605-65-8
N,N,N',N'-Tetramethylphosphorodiamidic chloride

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

: 5-chloroquinolin-8-yl N,N,N’,N’-tetramethyldiamidophosphate

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;	94%

: 2746-25-0
p-Methoxybenzyl bromide

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

: 8-(4-methoxybenzyloxy)-5-chloroquinoline

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In water; acetone at 20℃; for 0.666667h;	93.1%

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

: 106-93-4
ethylene dibromide

: 1231156-92-5
7-chloro-2,3-dihydro-1-oxa-3a-azonia-phenalene bromide

Conditions

Conditions	Yield
With Amberlite IRA 402(OH) resin In water at 80℃; for 2h; Inert atmosphere;	93%
With Amberlite IRA 402(OH) In water at 30 - 80℃; Inert atmosphere;	93%

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

: 98-09-9
benzenesulfonyl chloride

: 5-chloroquinolin-8-yl benzenesulfonate

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In water; acetone at 20℃; for 0.583333h;	92.6%

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

: 28188-41-2
3-(bromomethyl)benzonitrile

: 3-((5-chloroquinolin-8-yloxy)methyl)benzonitrile

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In water; acetone at 20℃; for 0.666667h;	92.4%

: diiodo(p-cymene)ruthenium(II) dimer

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

: [(η6-p-cymene)Ru(5-chloro-8-hydroxyquinolinato)I]

Conditions

Conditions	Yield
In methanol	92.1%

5-Chloro-8-hydroxyquinoline Consensus Reports

Reported in EPA TSCA Inventory.

5-Chloro-8-hydroxyquinoline Specification

1. Introduction of 5-Chloro-8-hydroxyquinoline
5-Chloro-8-hydroxyquinoline, with the CAS registry number 130-16-5, is also known as Cloxiquine. It belongs to the product categories of Quinolines, Quinazolines and derivatives; Quinolines; Haloquinolines; Hydroxyquinolines; Pesticide Intermediates. Its EINECS registry number is 204-978-1. Its IUPAC name is called 5-chloroquinolin-8-ol. 5-Chloro-8-hydroxyquinoline is light green to grey powder which can be used in organic synthesis. In addition, its classification codes are Antibacterial; Mutation data.

2. Properties of 5-Chloro-8-hydroxyquinoline
(1)ACD/LogP: 3.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.19; (4)ACD/LogD (pH 7.4): 2.17; (5)ACD/BCF (pH 5.5): 17.09; (6)ACD/BCF (pH 7.4): 16.46; (7)ACD/KOC (pH 5.5): 153.88; (8)ACD/KOC (pH 7.4): 148.24; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.696; (13)Molar Refractivity: 48.96 cm³; (14)Molar Volume: 127.1 cm³; (15)Surface Tension: 61.5 dyne/cm; (16)Density: 1.412 g/cm³; (17)Flash Point: 164.7 °C; (18)Enthalpy of Vaporization: 61.65 kJ/mol; (19)Boiling Point: 348.7 °C at 760 mmHg; (20)Vapour Pressure: 2.46E-05 mmHg at 25°C.

3. Structure Descriptors of 5-Chloro-8-hydroxyquinoline
(1)Canonical SMILES: C1=CC2=C(C=CC(=C2N=C1)O)Cl
(2)InChI: InChI=1S/C9H6ClNO/c10-7-3-4-8(12)9-6(7)2-1-5-11-9/h1-5,12H
(3)InChIKey: CTQMJYWDVABFRZ-UHFFFAOYSA-N

4. Toxicity of 5-Chloro-8-hydroxyquinoline

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LDLo	oral	1200mg/kg (1200mg/kg)		Proceedings of the Society for Experimental Biology and Medicine. Vol. 28, Pg. 484, 1931.

5. Safety Information of 5-Chloro-8-hydroxyquinoline
Hazard Symbols: Irritant

Xi
Risk Codes:
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Description:
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.

6. Preparation of 5-Chloro-8-hydroxyquinoline
The 5-Chloro-8-quinolinol can be prepared by 5-bromo-quinolin-8-ol. This reaction will need reagent pyridine hydrochloride. The reaction time is 10 min with reaction temperature of 220 ℃. The yield is about 93%.

7. Use of 5-Chloro-8-hydroxyquinoline
5-Chloro-8-quinolinol can be used to produce 5-chloro-7-(3,6,12,15-tetraoxa-9,21-diaza-bicyclo[15.3.1]heneicosa-1(20),17(21),18-trien-9-ylmethyl)-quinolin-8-ol by heating. This reaction need solvent benzene with reaction time of 12 hours. The yield is about 58%.

8. Other details of 5-Chloro-8-hydroxyquinoline
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. You should avoid contacting it with skin and eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

Product Name

5-Chloro-8-hydroxyquinoline

Synthetic route

5-Chloro-8-hydroxyquinoline Consensus Reports

5-Chloro-8-hydroxyquinoline Specification

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