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148-24-3

Basic Information
CAS No.: 148-24-3
Name: 8-Hydroxyquinoline
Article Data: 163
Cas Database
Molecular Structure:
Molecular Structure of 148-24-3 (8-Hydroxyquinoline)
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: HarmfulXn
Risk Codes: 22-68-36/37/38
Safety: 45-36/37/39-26-36
Transport Information: N/A
PSA: 33.12000
LogP: 1.94040
Synthetic route
77037-85-5

8-Quinolinyl formate

A

148-24-3

8-quinolinol

B

RhClCO(PPh3)2

RhClCO(PPh3)2

Conditions
ConditionsYield
With RhCl(PPh3)3 In benzene at 40℃; for 1h; Product distribution; primer deut. isotop eff.;A 100%
B n/a
6640-50-2

1,2,3,4-tetrahydroquinolin-8-ol

148-24-3

8-quinolinol

Conditions
ConditionsYield
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%
52968-25-9

Bis-<8-chinolinyl>-carbonat

81494-56-6

2-Amino-1,1,3,3-tetramethoxypropan

A

148-24-3

8-quinolinol

B

2--1,1,3,3-tetramethoxypropan

Conditions
ConditionsYield
In chloroform 1.) r. t., 12 h, 2.) reflux, 10 h;A 97%
B 74%
95-55-6

2-amino-phenol

56-81-5

glycerol

148-24-3

8-quinolinol

Conditions
ConditionsYield
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
118-92-3

anthranilic acid

107-02-8

acrolein

148-24-3

8-quinolinol

Conditions
ConditionsYield
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%
95-55-6

2-amino-phenol

107-02-8

acrolein

88-75-5

2-hydroxynitrobenzene

148-24-3

8-quinolinol

Conditions
ConditionsYield
With formic acid at 95 - 100℃; for 2h; Concentration; Molecular sieve;95.6%
110288-09-0

7,8-Epoxy-7,8-dihydroquinoline

A

580-20-1

quinolin-7-ol

B

148-24-3

8-quinolinol

Conditions
ConditionsYield
With silica gel at 110℃; for 0.25h; isomerization;A 5%
B 95%

8-methoxymethoxy-quinoline

148-24-3

8-quinolinol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;94%
95-55-6

2-amino-phenol

56-81-5

glycerol

88-75-5

2-hydroxynitrobenzene

148-24-3

8-quinolinol

Conditions
ConditionsYield
With nickel(III) oxide; sulfuric acid; acetic acid at 90℃; for 5h; Temperature;92.7%
With sulfuric acid; acetic acid
108530-08-1

quinolin-8-yl trifluoromethanesulfonate

148-24-3

8-quinolinol

Conditions
ConditionsYield
With caesium carbonate In toluene at 80℃; for 15h;92%
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    8-Hydroxyquinoline CAS No.:148-24-3 Name 8-Hydroxyquinoline Synonyms 8-Quinolinol; Quinolin-8-ol; Oxine Molecular Structure Molecular Formula C9H7NO Molecular Weight 145.16 CAS Registry Number 148-24

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    Molecular formula: C9H7NO Molecular weight: 145.16 CAS NO.: 148-24-3 Appearance:

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    Product Name: 8-Hydroxyquinoline CAS: 148-24-3 MF: C9H7NO MW: 145.16 EINECS: 205-711-1 Mol File: 148-24-3.mol 8-Hydroxyquinoline Structure 8-Hydroxyquinoline Chemical Properties Melting point 70-73 °C(lit.) Boiling point

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Analytical Methods

It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.

Specification

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%.

8-Hydroxyquinoline can be prepared by quinoline

Uses of 8-Hydroxyquinoline: it can be used to produce 8-butoxy-quinoline. This reaction will need reagent ethanol and KOH-solution.

8-Hydroxyquinoline can be used to produce 8-butoxy-quinoline

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.