8-Hydroxyquinoline
- CAS No.
- 148-24-3
- Chemical Name:
- 8-Hydroxyquinoline
- Synonyms
- OQ;8-OQ;Oxin;Tumex;OXINE;8-Oxine;BIOQUIN;8-Quinol;Fennosan;NSC 2039
- CBNumber:
- CB8435187
- Molecular Formula:
- C9H7NO
- Formula Weight:
- 145.16
- MOL File:
- 148-24-3.mol
- MSDS File:
- SDS
- 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
- 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 |
|
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 | 250 g | $270 | 2022-05-15 | Buy |
| Sigma-Aldrich | 8.20261 | 8-Hydroxyquinoline for synthesis | 148-24-3 | 25 kg | $1554 | 2021-12-16 | Buy |
| Sigma-Aldrich | 8.20261 | 8-Hydroxyquinoline for synthesis | 148-24-3 | 1 kg | $171.12 | 2021-12-16 | 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).
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).
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.
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.]
8-Hydroxyquinoline Preparation Products And Raw materials
Raw materials
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 23035 | 58 |
| Zhengzhou Yuanli Biological Technology Co., Ltd | 0086-371-67897895 | info@zzyuanli.cn | CHINA | 136 | 58 |
| Hefei TNJ Chemical Industry Co.,Ltd. | 0551-65418679 | info@tnjchem.com | China | 2995 | 55 |
| Tangshan Moneide Trading Co., Ltd. | 315-8309571 +8615633399667 | sales@moneidechem.com | CHINA | 545 | 58 |
| Career Henan Chemica Co | +86-0371-55982848 | laboratory@coreychem.com | China | 30290 | 58 |
| Wuhan Shuokang Biological Technology Co.，Ltd | 027-87366298 +8615927270571 | tianyi@skbiology.cn | CHINA | 296 | 58 |
| Shanghai UCHEM Inc. | +8615502138767 | sales@myuchem.com | China | 4099 | 58 |
| Springchem New Material Technology Co.,Limited | 021-62885108 +8613917661608 | info@spring-chem.com | China | 2064 | 57 |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 19994 | 60 |
| Henan DaKen Chemical CO.,LTD. | 371-66670886 | info@dakenchem.com | China | 15400 | 58 |
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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-Hydroxyquinoline
148-24-3
- US $0.00 / Kg/Drum
- ≥99.5%
- Jinan Finer Chemical Co., Ltd
-
- 8-Hydroxyquinoline
148-24-3
- US $15.00 / KG
- 99%
- Shanxi Lianxu New Material Co., LTD
-
- 8-Hydroxyquinoline Joyce
148-24-3
- US $19.90 / KG
- 99%
- Xingtai Haoxun Import and Export Trade Co., Ltd.
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