Back to ChemicalBook Home--->CAS DataBase List--->148-24-3

148-24-3

148-24-3 Structure

148-24-3 Structure
IdentificationMore
[Name]

8-Hydroxyquinoline
[CAS]

148-24-3
[Synonyms]

8-HYDROXYQUINOLINE
8-HYDROXYQUINOLINE BASE
8-OXYQUINOLINE
8-QUINILINOL
8-QUINOLINOL
8-QUINOLINONE
BIOQUIN
HYDROXYQUINOLINE
OXINE
OXYQUINOLINE
QUINOPHENOL
TIMTEC-BB SBB009097
1-Azanaphthalene-8-ol
8-Chinolinol
8-Hydroxychinolin
8-hydroxy-chinolin
8-hydroxy-quinolin
8-OQ
8-Oxyquinolin
8-Quinol
[EINECS(EC#)]

205-711-1
[Molecular Formula]

C9H7NO
[MDL Number]

MFCD00006807
[Molecular Weight]

145.16
[MOL File]

148-24-3.mol
Chemical PropertiesBack Directory
[Appearance]

Cream-colored crystals
[Melting point ]

70-73 °C(lit.)
[mp ]

70-73 °C(lit.)
[Boiling point ]

267 °C752 mm Hg(lit.)
[bp ]

267 °C752 mm Hg(lit.)
[density ]

1.0340
[refractive index ]

1.4500 (estimate)
[Fp ]

267°C
[storage temp. ]

Store at RT.
[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
[Detection Methods]

GC,NMR
[BRN ]

114512
[InChIKey]

MCJGNVYPOGVAJF-UHFFFAOYSA-N
[CAS DataBase Reference]

148-24-3(CAS DataBase Reference)
[NIST Chemistry Reference]

8-Quinolinol(148-24-3)
[IARC]

3 (Vol. 13, Sup 7) 1987
[Storage Precautions]

Light sensitive
[EPA Substance Registry System]

148-24-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R68:Possible risk of irreversible effects.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

2811
[WGK Germany ]

3
[RTECS ]

VC4200000
[Hazard Note ]

Harmful/Irritant
[TSCA ]

Yes
[HazardClass ]

9
[PackingGroup ]

III
[HS Code ]

29334990
[Safety Profile]

Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Experimental reproductive effects. A central nervous system stimulant. Human mutation data reported. Combustible when exposed to heat or flame. When heated to decomposition it emits hghly toxic fumes of NOx.
[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).
Raw materials And Preparation ProductsBack Directory
【Raw materials】

FUMING SULFURIC ACID-->Glycerol-->Quinoline-->2-Aminophenol-->2-Nitrophenol-->Sulfuric acid
【Preparation Products】

5-Methoxymethyl-2,3-pyridinedicarboxylic acid-->8-HYDROXYQUINOLINE-2-CARBOXYLIC ACID-->ribonucleic acid for injection-->Copper quinolate-->8-HYDROXYQUINOLINE-2-CARBONITRILE-->Chiniofon-->8-hydroxyquinoline dithiophosphate complex-->5,7-Dichloro-8-hydroxyquinoline-->8-Hydroxyquinoline-5-sulfonic acid-->5,7-Diiodo-8-quinolinol-->5,7-DIBROMO-8-HYDROXYQUINOLINE-->5-Chloro-8-hydroxyquinoline-->8-hydroxy-decahydroquinoline-->6,7-dichloroquinoline-5,8-dione-->2-Naphthalenesulfonic acid, 4-hydroxy-3-[(2-hydroxy-4-nitrophenyl)azo]-7-[(8-hydroxy-5-quinolinyl)azo]-, monosodium salt-->[4-Chloro-2-[[1-hydroxy-6-[[4-[(8-hydroxy-5-quinolinyl)azo]benzoyl]amino]-3-sulfo-2-naphtyl]azo]phenoxy]acetic acid-->Chromium, 3-[(8-hydroxy-5-quinolinyl)azo]benzenesulfonic acid complex-->Mordant Orange 26
Hazard InformationBack Directory
[General Description]

White to off-white or faintly yellow crystalline powder. Phenolic odor.
[Reactivity Profile]

8-HYDROXYQUINOLINE(148-24-3) darkens on exposure to light. This chemical readily forms stable metal chelates. 8-HYDROXYQUINOLINE(148-24-3) is incompatible with strong oxidizers. 8-HYDROXYQUINOLINE(148-24-3) is also incompatible with many metal ions.
[Air & Water Reactions]

Insoluble in water.
[Hazard]

Toxic by ingestion. Questionable carcinogen.
[Fire Hazard]

Flash point data for this chemical are not available; however, 8-HYDROXYQUINOLINE is probably combustible.
[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).
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).
[Uses]

Oxine is an almost universal complexing agent; it reacts with very many metal ions to give water-insoluble precipitates. It has been used so far for the determination of aluminium, antimony, beryllium, bismuth, cadmium, cerium, cobalt, chromium, copper, gallium, germanium, lanthanum, lithium, magnesium, manganese, molybdenum, nickel, ruthenium, thorium, titanium, uranium, vanadium, tungsten, zinc and zirconium.
With the exception of the aluminium, bismuth, gallium, indium, lead and thallium complexes, the oxinate precipitates contain water of crystallization. The majority of the complexes are of stoichiometric composition (either with or without water of crystallization), and therefore subsequent to drying at suitable temperature the precipitates are ready for direct weighing. The precipitates containing water of crystallization are usually dried at 100-105°C and weighed as such, or dried at 130-140°C when the water of crystallization is eliminated.
The complexes can be decomposed with strong acids, and the oxine liberated in an amount equivalent to the metal may be determined by bromatometric titration.
The electrically neutral oxinate complexes are sparingly soluble in water whereas they readily dissolve in apolar solvents immiscible with water, for instance chloroform. Hence this ligand is useful for the solvent extraction enrichment and the subsequent spectrophotometric determination of metal ions. The optimum pH range for complex formation is dependent upon the stabilities of the oxinate complexes. Accordingly, divalent metals are usually precipitated quantitatively in neutral or slightly alkaline media. Adjustment of the suitable pH may be made with various tartrate buffers, for example with ammonia-ammonium tartrate in the pH range 6-10, and with sodium hydroxidesodium tartrate buffers for the pH range 10-13. Complexes of tri- and tetravalent metals are more stable, and thus can be precipitated quantitatively even at about pH 4. In these cases the pH of the solution is adjusted to the desired value with acetic acid-sodium acetate buffers. The copper(II) and iron(III) complexes precipitate quantitatively even at pH 2.7, as does vanadium(V) as an oxinate complex of uncertain composition.
[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)
[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.
[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.]
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

8-Quinolinol(148-24-3).msds
Spectrum DetailBack Directory
[Spectrum Detail]

8-Hydroxyquinoline(148-24-3) Raman
8-Hydroxyquinoline(148-24-3) 1H NMR
8-Hydroxyquinoline(148-24-3) MS
8-Hydroxyquinoline(148-24-3) 13C NMR
8-Hydroxyquinoline(148-24-3) IR1
8-Hydroxyquinoline(148-24-3) IR2
8-Hydroxyquinoline(148-24-3) ESR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

8-Hydroxyquinoline, for analysis ACS(148-24-3)
[Alfa Aesar]

8-Hydroxyquinoline, ACS(148-24-3)
[Sigma Aldrich]

148-24-3(sigmaaldrich)
[TCI AMERICA]

8-Quinolinol,>99.0%(GC)(T)(148-24-3)
148-24-3 suppliers list
Company Name: Hubei xin bonus chemical co. LTD
Tel: 86-13657291602
Fax: 027-59338440
Website: www.chemicalbook.com/ShowSupplierProductsList1549548/0.htm
Company Name: Zhengzhou Yuanli Biological Technology Co., Ltd
Tel: 0086-371-67897895
Fax:
Website: www.yonlytech.com
Company Name: Hefei TNJ Chemical Industry Co.,Ltd.
Tel: 86-0551-65418684 18949823763
Fax: 86-0551-65418684
Website: www.tnjchem.com
Company Name: Tangshan Moneide Trading Co., Ltd.
Tel: 86-315-8309571 15633399667
Fax:
Website: www.moneidechem.com
Company Name: Career Henan Chemica Co
Tel: 0371-86658258 , 13203830695
Fax: 0371-86658258
Website: www.coreychem.com/index.html
Company Name: Wuhan Shuokang Biological Technology Co.,Ltd
Tel: +86-86-02787366298 , +8615927270571
Fax:
Website:
Company Name: Springchem New Material Technology Co.,Limited
Tel: +86-021-62885108 , +8613917661608
Fax:
Website: www.spring-chem.com
Company Name: Capot Chemical Co.,Ltd.
Tel: +86-571-85586718 , +86(0)13336195806
Fax: +86-571-85864795
Website: http://www.capotchem.com
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: 0371-55170693
Fax: 0371-55170693
Website: www.tianfuchem.net
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008615858145714
Fax: +86-571-56059825
Website: www.fandachem.com
Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +86 21 5161 9050/ 5187 7795
Fax: +86 21 5161 9052/ 5187 7796
Website: www.atkchemical.com
Company Name: career henan chemical co
Tel: +86-371-86658258
Fax:
Website: www.coreychem.com/index.html
Company Name: NINGBO INNO PHARMCHEM CO., LTD.
Tel: 13867897135
Fax:
Website: en.nbinno.com
Company Name: Hubei Jusheng Technology Co.,Ltd.
Tel: 86-18871470254
Fax: 027-59599243
Website: www.hubeijusheng.com
Company Name: Hebei Guanlang Biotechnology Co., Ltd.
Tel: +8619930503282
Fax:
Website: www.chemicalbook.com/ShowSupplierProductsList31448/0.htm
Company Name: Shanghai Worldyang Chemical Co.,Ltd.
Tel: +86-13651600618;+86-21-56795779
Fax:
Website: www.chemicalbook.com/ShowSupplierProductsList1875604/0.htm
Company Name: Chongqing Chemdad Co.,Ltd
Tel: +86-19923101450
Fax:
Website: www.chemdad.com
Company Name: Xiamen AmoyChem Co., Ltd
Tel: +86 592-605 1114
Fax:
Website: www.amoychem.com
Tags:148-24-3 Related Product Information
4965-36-0 91-22-5 35853-41-9 492-27-3 343-10-2 71083-06-2 4510-76-3 42712-64-1 86-95-3 15733-89-8 15450-76-7 86-99-7 84-88-8 7246-07-3 59-00-7 773-76-2 2598-29-0 21302-43-2