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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
Molecular Weight:
145.16
MOL File:
148-24-3.mol
MSDS File:
SDS

8-Hydroxyquinoline Properties

Melting point 70-73 °C(lit.)
Boiling point 267 °C752 mm Hg(lit.)
Density 1.0340
refractive index 1.4500 (estimate)
Flash point 267°C
storage temp. Store below +30°C.
solubility 0.56g/l
form Liquid
pka 5.017(at 20℃)
color White to pale yellow or light beige
Water Solubility INSOLUBLE
Sensitive Light Sensitive
Merck 14,4843
BRN 114512
InChIKey MCJGNVYPOGVAJF-UHFFFAOYSA-N
CAS DataBase Reference 148-24-3(CAS DataBase Reference)
FDA 21 CFR 310.545
EWG's Food Scores 1-3
FDA UNII 5UTX5635HP
ATC code A01AB07,D08AH03,G01AC30,R02AA14
IARC 3 (Vol. 13, Sup 7) 1987
NIST Chemistry Reference 8-Quinolinol(148-24-3)
EPA Substance Registry System 8-Quinolinol (148-24-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H341
Precautionary statements  P201-P280-P301+P312a-P308+P313-P405-P501a
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
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).
NFPA 704
1
2 0

8-Hydroxyquinoline price More Price(61)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 252565 8-Hydroxyquinoline ACS reagent, 99% 148-24-3 50g $66.4 2022-05-15 Buy
Sigma-Aldrich 252565 8-Hydroxyquinoline ACS reagent, 99% 148-24-3 1kg $284 2022-05-15 Buy
Sigma-Aldrich 1.07098 8-Hydroxyquinoline GR for analysis Reag. Ph Eur 148-24-3 250g $270 2022-05-15 Buy
Sigma-Aldrich 8.20261 8-Hydroxyquinoline for synthesis 148-24-3 1kg $171.12 2021-12-16 Buy
Sigma-Aldrich 8.20261 8-Hydroxyquinoline for synthesis 148-24-3 25kg $1554 2021-12-16 Buy
Product number Packaging Price Buy
252565 50g $66.4 Buy
252565 1kg $284 Buy
1.07098 250g $270 Buy
8.20261 1kg $171.12 Buy
8.20261 25kg $1554 Buy

8-Hydroxyquinoline Chemical Properties,Uses,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: 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.

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).

Manufacturing Process

The mixture of 1.4 kg o-nitrophenol, 2.1 kg o-aminophenol, 6 kg glycerine (d = 1.26) and 5 kg sulfuric acid (d = 1.848) was heated at reflux to temperature 130°-140°C. This temperature was kept for 1.5 hours. The obtained oxyquinoline precipitated, the liquid was removed with water-steam distillation. The residue was diluted with water and alkalized with sodium hydroxide and sodium carbonate to the strong alkaline reaction. The repeated distillation with water steam gave the oil, which hardened as the long needles by cooling. MP: 75°-76°C recrystallized from diluted ethanol.
In practice it is usually used as sulfate salt

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.

Fire Hazard

Flash point data for 8-Hydroxyquinoline are not available; however, 8-Hydroxyquinoline is probably combustible.

Biochem/physiol Actions

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

Oxine, quinophenol, or oxyquinoline is the parent compoundfrom which the antiprotozoal oxyquinolines havebeen derived. The antibacterial and antifungal properties of oxine and its derivatives, which are believed to result fromthe ability to chelate metal ions, are well known. Aqueoussolutions of acid salts of oxine, particularly the sulfate(Chinosol, Quinosol), in concentrations of 1:3,000 to1:1,000, have been used as topical antiseptics. The substitutionof an iodine atom at the 7-position of 8-hydroxyquinolinesyields compounds with broad-spectrum amebicidalproperties.

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.]

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View Lastest Price from 8-Hydroxyquinoline manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-02-25 8-Hydroxyquinoline
148-24-3
US $0.00 / Kg/Drum 1KG ≥99.5% 500mt Jinan Finer Chemical Co., Ltd
2022-02-24 8-Hydroxyquinoline
148-24-3
US $15.00 / KG 1KG 99% 1000kg/month Shanxi Lianxu New Material Co., LTD
2022-02-24 8-Hydroxyquinoline Joyce
148-24-3
US $19.90 / KG 10g 99% 10 tons Xingtai Haoxun Import and Export Trade Co., Ltd.
8-hydroxy-quinolin 8-OQ 8-Oxyquinolin 8-Quinol 8-Quinolol Fennosan Fennosan H 30 fennosanh30 fennosanhf-15 Hydroxybenzopyridine NCI-C55298 NCL-C55298 o-Oxychinolin Oxin Oxoquinoline Oxybenzopyridine Oxychinolin Oxychinoline Phenopyridine quinoline,8-hydroxy- Tumex USAF ek-794 usafek-794 Azanaphthalene-8-ol Hydroxychinolin OQ 8 HYDROXY QUINOLINE MIN 8- HYDRO OXY QUINOLINE 8-HYDROXYQUINOLINE 99% A.C.S. REAGENT 8-Hydroxyquinoline (technical) 8-Quinolinol (technical) Oxyquinoline (technical) 8-Hydroxyquinoline, reagent ACS 8-QUINOLINOL ACS REAGENT 8-HYDROXYQUINOLINE PESTANAL, 250 MG 8-HYDROXYQUINOLINE, 99+% 8-HYDROXYQUINOLINE, 1GM, NEAT 8-HYDROXYQUINOLINE R. G., REAG. ACS,REAG . PH. EUR. 8-QUINOLINOL, ACS 8-HYDROXYQUINOLINE GR ACS 99.5+% 8-HYDROXYQUINOLINE99.8% ORGANIC ANALYTICAL STANDARD 8-Hydroxyquinoline-(8-Quinolinol,Oxine) 8-Hydroxyquinoline(Oxine) 8-HydroxyquinolineGr-(8-Quinolinol,Oxine) 8-HydroxyquinolineA.R. 8-HydroxyquinolineGr ORTHO-OXYQUINOLINE HYDROXY-8-QUINOLINE 8-HYDROXYQUINOLINEANDITSSULPHATE NSC 2039 NSC 285166 NSC 402623 8-hydroxyquinoline, acs 8-QUINOLINOL,CRYSTAL,REAGENT,ACS 8-Hydroxyquinoline Oxine 8-Quinolinone Quinophenol 8-HYDROXYQUINOLINE GR FOR ANALYSIS ACS 8-Hydroxyprolineine 8-Quinolinol >=99% (perchloric acid titration)