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5-Chloro-8-hydroxyquinoline

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Name

5-Chloro-8-hydroxyquinoline

EINECS 204-978-1
CAS No. 130-16-5 Density 1.412 g/cm3
PSA 33.12000 LogP 2.59380
Solubility N/A 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 N/A Appearance light green to grey powder
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 130-16-5 (5-Chloro-8-hydroxyquinoline) Hazard Symbols IrritantXi
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-;

Article Data 31

5-Chloro-8-hydroxyquinoline Synthetic route

130-26-7

5-chloro-7-iodoquinolin-8-ol

130-16-5

5-Chloro-8-hydroxyquinoline

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sulfuryl dichloride; chloroform
89-64-5

p-chloro-o-nitrophenol

56-81-5

glycerol

130-16-5

5-Chloro-8-hydroxyquinoline

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride; water at 175℃;

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:IrritantXi
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.

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