ChemicalBook > CAS DataBase List > 8-Hydroxyquinoline

8-Hydroxyquinoline

Product Name
8-Hydroxyquinoline
CAS No.
148-24-3
Chemical Name
8-Hydroxyquinoline
Synonyms
Quinolin-8-ol;8-QUINOLINOL;OXINE;OXYQUINOLINE;HYDROXYQUINOLINE;8-OQ;8-Oxyquinolin;8-OXYQUINOLINE;Hydroxychinolin;8-Hydroxychinolin
CBNumber
CB8435187
Molecular Formula
C9H7NO
Formula Weight
145.16
MOL File
148-24-3.mol
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8-Hydroxyquinoline Property

Melting point:
70-73 °C(lit.)
Boiling point:
267 °C752 mm Hg(lit.)
Density 
1.0340
vapor pressure 
0.221Pa at 25℃
refractive index 
1.4500 (estimate)
Flash point:
267°C
storage temp. 
Store below +30°C.
solubility 
0.56g/l
pka
5.017(at 20℃)
form 
Liquid
color 
White to pale yellow or light beige
Water Solubility 
INSOLUBLE
Sensitive 
Light Sensitive
Merck 
14,4843
BRN 
114512
InChIKey
MCJGNVYPOGVAJF-UHFFFAOYSA-N
LogP
1.85 at 25℃
CAS DataBase Reference
148-24-3(CAS DataBase Reference)
NIST Chemistry Reference
8-Quinolinol(148-24-3)
IARC
3 (Vol. 13, Sup 7) 1987
EPA Substance Registry System
8-Quinolinol (148-24-3)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-68-36/37/38
Safety Statements 
45-36/37/39-26-36
RIDADR 
2811
WGK Germany 
3
RTECS 
VC4200000
Hazard Note 
Harmful/Irritant
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29334990
Hazardous Substances Data
148-24-3(Hazardous Substances Data)
Toxicity
An LD50 value of 1,200mg/kg was reported for oral administration of 8-hydroxyquinoline to rats (straidsex unspecified; AAPCO, 1966);a value of 48 mg/kg was reported for intraperitoneal administration to mice (strain/sex unspecxed; Bernstein et al., 1963).
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H317May cause an allergic skin reaction

H318Causes serious eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.20261
Product name
8-Hydroxyquinoline
Purity
for synthesis
Packaging
250g
Price
$71.8
Updated
2024/03/01
Sigma-Aldrich
Product number
8.20261
Product name
8-Hydroxyquinoline
Purity
for synthesis
Packaging
1kg
Price
$251
Updated
2024/03/01
Sigma-Aldrich
Product number
8.20261
Product name
8-Hydroxyquinoline
Purity
for synthesis
Packaging
25kg
Price
$2100
Updated
2024/03/01
Sigma-Aldrich
Product number
252565
Product name
8-Hydroxyquinoline
Purity
ACS reagent, 99%
Packaging
50g
Price
$76
Updated
2024/03/01
Sigma-Aldrich
Product number
252565
Product name
8-Hydroxyquinoline
Purity
ACS reagent, 99%
Packaging
1kg
Price
$266
Updated
2024/03/01
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8-Hydroxyquinoline Chemical Properties,Usage,Production

Chemical Properties

8-Hydroxyquinoline is a white to cream-colored crystal or crystalline powder that is insoluble in water or ether and freely soluble in ethanol, acetone, chloroform, benzene, and aqueous mineral acids. It readily forms stable metal chelates, which are soluble or precipitable in organic solvents, depending on the pH of the solution (Hollingshead, 1954).

Originator

Chinosol,Chinosolfabrik

Uses

8-Hydroxyquinoline has a wide variety of uses. Primarily because of their metal chelating properties, 8-hydroxyquinoline and its salts, halogenated derivatives, and metal complexes have been used as analytical reagents (Hollingshead, 1954) and as antimicrobial agents in medicine, fungicides, and insecticides (Harvey, 1975). It is also used as a preservative in cosmetics and tobacco, a chemical intermediate in dye synthesis (IARC, 1977), and a precipitating reagent for uranium and other radioactive metals in nuclear power plant liquid waste effluent. It is used in nuclear medicine with indium-111 (Davis et al., 1978).

Definition

ChEBI: 8-Hydroxyquinoline is a monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes. It has a role as an antibacterial agent, an iron chelator, an antiseptic drug and an antifungal agrochemical. It derives from a hydride of a quinoline.

Application

8-Hydroxyquinoline may be used as a chelating ligand in the preparation of tris-(8-hydroxyquinoline)aluminum (Alq3), an organic electroluminescent compound used in organic light-emitting devices (OLEDs).

Preparation

8-Hydroxyquinoline is synthesized from o-aminophenol by cyclization reaction. Add glycerin into the acid-resistant reaction pot, slowly add concentrated sulfuric acid under stirring, and simultaneously add o-aminophenol and o-nitrophenol in sequence, and add 65% of the total oleum first. Heat up to 125°C, stop heating, naturally heat up to 140°C, and wait until the temperature returns to 136°C. The rest of the oleum was continued to be added, maintaining the temperature at 137°C. After adding acid, keep warm for 4 hours, cool to below 100°C, pump into an acid-resistant pot containing 10 times the amount of water (calculated by o-aminophenol), stir, heat to 75-80°C, use 30% sodium hydroxide The solution was neutralized to pH 7-7.2. The precipitate is released while hot, cooled into a block, and sublimed under reduced pressure to obtain the finished product of 8-hydroxyquinoline.

brand name

Aci-jel;Benzease;Chinosol;Cp-cap;Dermacid;Dermoplast;Fennosan h 30;Heriat;Hydroxybenoxopyridine;Medicone derma-hc;Oxykin;Oxyquinoline-rhp;Pedivol;Phenopyridine;Preconsol;Quinoderm;Quinoped;Quinophenol;Recta medicone-hc;Semori;Serohinol;Serorhinol;Superol;Trimo-san;Triva douch powder;Triva jel.

Therapeutic Function

Antiseptic

World Health Organization (WHO)

Halogenated hydroxyquinoline is structurally related to clioquinol. See WHO comment for clioquinol. (Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)

General Description

White to off-white or faintly yellow crystalline powder. Phenolic odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

8-Hydroxyquinoline darkens on exposure to light. 8-Hydroxyquinoline readily forms stable metal chelates. 8-Hydroxyquinoline is incompatible with strong oxidizers. 8-Hydroxyquinoline is also incompatible with many metal ions.

Hazard

Toxic by ingestion. Questionable carcinogen.

Biochem/physiol Actions

8-Hydroxyquinoline is a RNA synthesis inhibitor that acts as a fungicide against Trichophyton mentagrophytes, Myrothecium verrucaria, and Trichoderma viride. The antifungal mechanism of action is not clear but appears to be structurally related.

Clinical Use

8-Hydroxyquinoline (8HQ) is an intermediate of halogenated quinoline anti-amebic drugs, including quiniodoform, clioquinoline, diiodoquinoline and the like. These drugs exert anti-amebic effects by inhibiting intestinal commensal bacteria, and are effective against amoebic dysentery, but have no effect on extra-intestinal amoebic parasites.8HQ is a small planar molecule with a lipophilic effect and a metal chelating ability. As a result, 8HQ and its derivatives hold medicinal properties such as antineurodegenerative, anticancer, antioxidant, antimicrobial, anti-inflammatory, and antidiabetic activities.

Safety Profile

8-Hydroxyquinoline (8-HQ) may be a skin irritant in man. Hair depigmentation was seen in mice treated dermally. Dilute solutions were slightly irritating to the eyes of rabbits. In cases of human poisoning (by ingestion or by the administration of an enema containing 8-HQ or its sulphate), the kidney, liver and blood were the principal sites of toxic attack. Comprehensive studies involving repeated oral administration of 8-HQ to rodents failed to identify any particular sites for toxic attack and provided no convincing evidence of carcinogenicity. 8-HQ induced chromosomal damage in mammalian cells in culture (including human cells), but gave conflicting results in mice treated intraperitoneally. Both 8-HQ and its sulphate have induced mutagenicity in Ames bacterial tests and there was some evidence of mutagenic activity in mammalian cells treated in culture.

Purification Methods

Crystallise oxine from hot EtOH, acetone, pet ether (b 60-80o) or water. Crude oxine can be purified by precipitation of copper oxinate, followed by liberation of free oxine with H2S or by steam distillation after acidification with H2SO4. Store it in the dark. It forms complexes with many metals. [Manske et al. Can J Research 27F 359 1949, Phillips Chem Rev 56 271 1956, Beilstein 21 III/IV 1135, 21/3 V 252.]

8-Hydroxyquinoline Preparation Products And Raw materials

Raw materials

FUMING SULFURIC ACID Quinoline 2-Nitrophenol Glycerol 2-Aminophenol

Preparation Products

8-HYDROXYQUINOLINE-2-CARBOXYLIC ACID 8-Hydroxyquinoline-5-sulfonic acid 8-hydroxyquinoline dithiophosphate complex 5,7-Diiodo-8-quinolinol 5-Methoxymethyl-2,3-pyridinedicarboxylic acid ribonucleic acid for injection 8-HYDROXYQUINOLINE-2-CARBONITRILE 5-Chloro-8-hydroxyquinoline Copper quinolate Chiniofon 5,7-Dichloro-8-hydroxyquinoline 5,7-DIBROMO-8-HYDROXYQUINOLINE
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View Lastest Price from 8-Hydroxyquinoline manufacturers

Hebei Andu Technology Com.,Ltd
Product
8-Hydroxyquinoline 148-24-3
Price
US $3.50/kg
Min. Order
1kg
Purity
≥99%
Supply Ability
3000tons/month
Release date
2024-08-17
Dorne Chemical Technology co. LTD
Product
8-Hydroxyquinoline 148-24-3
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
WUHAN FORTUNA CHEMICAL CO., LTD
Product
8-Hydroxyquinoline 148-24-3
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-12

148-24-3, 8-HydroxyquinolineRelated Search:

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