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| CAS No.: | 130-16-5 |
|---|---|
| Name: | 5-Chloro-8-hydroxyquinoline |
| Molecular Structure: | |
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|
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| Formula: | C9H6ClNO |
| Molecular Weight: | 179.606 |
| 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-; |
| EINECS: | 204-978-1 |
| Density: | 1.412 g/cm3 |
| Melting Point: | 122-124 °C(lit.) |
| Boiling Point: | 348.7 °C at 760 mmHg |
| Flash Point: | 164.7 °C |
| Appearance: | light green to grey powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36-24/25 |
| PSA: | 33.12000 |
| LogP: | 2.59380 |
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| 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% |
| 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 | Yield |
|---|---|
| With pyridine; water Heating; | 92% |
| Multi-step reaction with 2 steps 1: NaOH / Heating 2: 94 percent / pyridine / 4 h / Heating View Scheme |
| 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 | Yield |
|---|---|
| With hydrogenchloride In water at 111℃; for 24h; Doebner-von Miller Reaction; | 49% |
| 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 | Yield |
|---|---|
| With sulfuryl dichloride; chloroform |
| Conditions | Yield |
|---|---|
| With formic acid; sulfuric acid | |
| With sulfuric acid; acetic acid | |
| With phosphoric acid; sulfuric acid |
| Conditions | Yield |
|---|---|
| With arsenic(V) oxide; sulfuric acid at 150 - 160℃; | |
| With sulfuric acid at 90℃; for 0.25h; |
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Consensus Reports
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:
XiRisk 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%.
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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%.
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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.