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| CAS No.: | 148-24-3 |
|---|---|
| Name: | 8-Hydroxyquinoline |
| Molecular Structure: | |
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| Formula: | C9H7NO |
| Molecular Weight: | 203.241 |
| Synonyms: | 8-Quinolinol;8-Chinolinol;8-Chinolinol [Czech];8-Hydroxy-chinolin [German];8-Quinol;Bioquin;CCRIS 340;Oxychinolin;Oxyquinoline;Phenopyridine;Quinoline, 8-hydroxy-; |
| EINECS: | 205-711-1 |
| Density: | 1.26 g/cm3 |
| Melting Point: | 70-73 °C(lit.) |
| Boiling Point: | 267 °C at 760 mmHg |
| Flash Point: | 143.1 °C |
| Solubility: | Insoluble in water |
| Appearance: | Cream-colored crystals |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-68-36/37/38 |
| Safety: | 45-36/37/39-26-36 |
| PSA: | 33.12000 |
| LogP: | 1.94040 |
| Conditions | Yield |
|---|---|
| With RhCl(PPh3)3 In benzene at 40℃; for 1h; Product distribution; primer deut. isotop eff.; | A 100% B n/a |
| Conditions | Yield |
|---|---|
| With potassium tert-butylate In decane at 150℃; for 36h; Inert atmosphere; Schlenk technique; | 98% |
| With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In acetonitrile at 100℃; under 11251.1 Torr; for 24h; Autoclave; | 93% |
| With perylene diimide covalent immobilized to SiO2 nanospheres; air In N,N-dimethyl acetamide at 20℃; UV-irradiation; | 93% |
Bis-<8-chinolinyl>-carbonat
2-Amino-1,1,3,3-tetramethoxypropan
A
8-quinolinol
| Conditions | Yield |
|---|---|
| In chloroform 1.) r. t., 12 h, 2.) reflux, 10 h; | A 97% B 74% |
| Conditions | Yield |
|---|---|
| Stage #1: glycerol With sulfuric acid; copper(II) sulfate; calcium oxide for 1h; Reflux; Stage #2: 2-amino-phenol for 0.333333h; Skraup Quinoline Synthesis; Stage #3: With 2-hydroxynitrobenzene at 130 - 140℃; Concentration; | 96.31% |
| Stage #1: 2-amino-phenol With sulfuric acid; 2-hydroxynitrobenzene at 70℃; for 0.5h; Stage #2: glycerol at 150℃; for 4h; Temperature; | 91% |
| With sulfuric acid In water at 36 - 200℃; for 0.25h; Microwave irradiation; Sealed tube; Green chemistry; | 34% |
| With sulfuric acid; iodine | |
| Stage #1: 2-amino-phenol; glycerol With sulfuric acid Stage #2: With nitrobenzene |
| Conditions | Yield |
|---|---|
| Stage #1: anthranilic acid; acrolein With hydrogenchloride; acetic acid; hydroquinone at 95 - 100℃; for 3h; Stage #2: With chloropyridinecobaloxime(III); Eosin Y In water; acetonitrile at 20℃; for 3h; Microwave irradiation; | 96.2% |
| Conditions | Yield |
|---|---|
| With formic acid at 95 - 100℃; for 2h; Concentration; Molecular sieve; | 95.6% |
| Conditions | Yield |
|---|---|
| With silica gel at 110℃; for 0.25h; isomerization; | A 5% B 95% |
8-quinolinol
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry; | 94% |
| Conditions | Yield |
|---|---|
| With nickel(III) oxide; sulfuric acid; acetic acid at 90℃; for 5h; Temperature; | 92.7% |
| With sulfuric acid; acetic acid |
quinolin-8-yl trifluoromethanesulfonate
8-quinolinol
| Conditions | Yield |
|---|---|
| With caesium carbonate In toluene at 80℃; for 15h; | 92% |
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It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.
The 8-Hydroxyquinoline, also known as 8-Quinolinol, is the organic compound with the formula C9H7NO. It belongs to the product categories of Inorganic & Organic Chemicals; Fine Chemical & Intermediates; Quinolines, Quinazolines and derivatives; Quinolines; Analytical Chemistry; Bipyridyls, etc. (Chelating Reagents); Chelating Reagents; Hydroxyquinolines; Pharmaceutical intermediates; Miscellaneous Compounds; Aromatics; Miscellaneous Reagents. Its EINECS registry number is 205-711-1. With the CAS registry number 148-24-3, its IUPAC name is quinolin-8-ol. This chemical is white to off-white or faintly yellow crystalline powder with phenolic odor. What's more, it is insoluble in water.
Physical properties of 8-Hydroxyquinoline: (1)ACD/LogP: 1.901; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.77; (4)ACD/LogD (pH 7.4): 0.82; (5)ACD/BCF (pH 5.5): 1.23; (6)ACD/BCF (pH 7.4): 1.35; (7)ACD/KOC (pH 5.5): 19.25; (8)ACD/KOC (pH 7.4): 21.28; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.691; (13)Molar Refractivity: 44.068 cm3; (14)Molar Volume: 115.203 cm3; (15)Surface Tension: 59.73 dyne/cm; (16)Density: 1.26 g/cm3; (17)Flash Point: 143.07 °C; (18)Enthalpy of Vaporization: 52.536 kJ/mol; (19)Boiling Point: 266.999 °C at 760 mmHg
Preparation: It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol. This chemical can also be prepared by quinoline. This reaction will need reagent O3, isopentyl alcohol and solvent H2O. The reaction temperature is -0.1 °C. The yield is about 78%.
Uses of 8-Hydroxyquinoline: it can be used to produce 8-butoxy-quinoline. This reaction will need reagent ethanol and KOH-solution.
This colorless compound is widely used commercially, although under a variety of names. Solution of 8-Hydroxyquinoline in alcohol is used as liquid bandages. It once was of interest as an anti-cancer drug. The reaction of 8-Hydroxyquinoline with aluminium(III) results in Alq3, a common component of organic light-emitting diodes (OLED's). Variations in the substituents on the quinoline rings affect its luminescence properties. The roots of the invasive plant Centaurea diffusa release 8-Hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it.
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. 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, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)InChI: InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
(2)InChIKey: MCJGNVYPOGVAJF-UHFFFAOYSA-N
(3)Canonical SMILES : C1=CC2=C(C(=C1)O)N=CC=C2
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD20 | oral | 1205mg/kg (1205mg/kg) | Teratology, The International Journal of Abnormal Development. Vol. 20, Pg. 413, 1979. | |
| mammal (species unspecified) | LD50 | unreported | 1gm/kg (1000mg/kg) | "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 410, 1971. | |
| mouse | LD50 | intraperitoneal | 43mg/kg (43mg/kg) | Farmakologiya i Toksikologiya Vol. 42, Pg. 396, 1979. | |
| mouse | LD50 | oral | 20gm/kg (20000mg/kg) | Drugs in Japan Vol. 6, Pg. 271, 1982. | |
| mouse | LD50 | subcutaneous | 83600ug/kg (83.6mg/kg) | Pharmazie. Vol. 1, Pg. 150, 1946. | |
| rat | LC50 | inhalation | > 1210mg/m3/6H (1210mg/m3) | Journal of the American College of Toxicology. Vol. 11, Pg. 497, 1992. | |
| rat | LD50 | oral | 1200mg/kg (1200mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 602, 1966. |
