8-Hydroxyquinoline
- Iupac Name：quinolin-8-ol
- CAS No.: 148-24-3
- Molecular Weight：145.15798
- Modify Date.: 2022-11-07 12:38
- Introduction: 8-Hydroxyquinoline, with the chemical formula C9H7NO and CAS registry number 148-24-3, is a heterocyclic organic compound. This yellowish-white crystalline solid with phenolic odor is characterized by its quinoline ring fused with a hydroxyl group at the 8-position. It finds applications in various fields including pharmaceuticals, analytical chemistry, and as a precursor in organic synthesis. 8-Hydroxyquinoline exhibits chelating properties, forming complexes with metal ions, making it useful in metal ion detection and extraction. It is also utilized as an antiseptic, fungicide, and corrosion inhibitor. Additionally, derivatives of 8-hydroxyquinoline are investigated for their potential therapeutic applications, including as antimicrobial agents and in the treatment of neurodegenerative diseases.
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1. Names and Identifiers
- 1.1 Name
- 8-Hydroxyquinoline
- 1.2 Synonyms
(8-hydroxy)quinoline 8-hydroxy-quinolin 8-hydroxy-quinoline 8-OH-quinoline 8-OQ 8-Oxychinolin 8-Oxyquinolin 8-oxyquinoline 8-Quinol 8-Quinolinol 8-Quinolinone 8-Quinolol EINECS 205-711-1 Fennosan Fennosan H 30 fennosanh30 MFCD00006807 Oxine oxybenzopyridine oxychinolin Quinolin-8-ol Quinophenol T66 BNJ JQ Tumex
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- 1.3 CAS No.
- 148-24-3
- 1.4 CID
- 1923
- 1.5 EINECS(EC#)
- 205-711-1
- 1.6 Molecular Formula
- C9H7NO (isomer)
- 1.7 Inchi
- InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
- 1.8 InChIkey
- MCJGNVYPOGVAJF-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC2=C(C(=C1)O)N=CC=C2
- 1.10 Isomers Smiles
- C1=CC2=C(C(=C1)O)N=CC=C2
2. Properties
- 2.1 Density
- 1.03
- 2.1 Melting point
- 70-74℃
- 2.1 Boiling point
- 267℃ (752 mmHg)
- 2.1 Refractive index
- 1.4500 (estimate)
- 2.1 Flash Point
- 100 °C
- 2.1 Precise Quality
- 145.05300
- 2.1 PSA
- 33.12000
- 2.1 logP
- 1.94040
- 2.1 Solubility
- 0.56g/l
- 2.2 Appearance
- White Crystal
- 2.3 Storage
- Light Sensitive. Ambient temperatures.
- 2.4 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).
- 2.5 Color/Form
- White crystals or white crystalline powder
- 2.6 Decomposition
- WHEN HEATED TO DECOMP EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES/.
- 2.7 Odor
- Phenolic odor
- 2.8 pKa
- 5.017(at 20℃)
- 2.9 Water Solubility
- INSOLUBLE
- 2.10 Spectral Properties
- SADTLER REF NUMBER: 187 (IR, PRISM); 63 (IR, GRATING); MAX ABSORPTION (ALCOHOL): 240 NM (LOG E= 4.60); 308 NM (LOG E= 3.47)
Intense mass spectral peaks: 145 m/z (100%), 117 m/z (78%), 90 m/z (30%), 89 m/z (29%)
IR: 5568 (Coblentz Society Spectral Collection)
UV: 76 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 24 (Sadtler Research Laboratories Spectral Collection)
MASS: 65043 (NIST/MSDC/EPA Mass Spectral Database, 1990 version)
- 2.11 Stability
- Stable. Combustible. Incompatible with strong oxidizing agents,many metal ions. Readily forms chelates.
- 2.12 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 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.
- 3.2 General Description
- White to off-white or faintly yellow crystalline powder. Phenolic odor.
- 3.3 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
- 3.4 Usage
-
Microbiocide, fungicide.
4. Safety and Handling
- 4.1 Symbol
- GHS07;
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R22;R36/37/38;R68
- 4.1 Safety Statements
- S26;S36/37/39;S45
- 4.1 Packing Group
- III
- 4.1 Octanol/Water Partition Coefficient
- log Kow = 2.02
- 4.2 Fire Hazard
- Flash point data for 8-Hydroxyquinoline are not available; however, 8-Hydroxyquinoline is probably combustible.
- 4.3 Hazard Class
- 9
- 4.3 Hazard Declaration
- H302
- 4.3 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.4 RIDADR
- OTH
- 4.4 FirePotential
- Combustible when exposed to heat or flame.
- 4.5 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.
- 4.6 Formulations/Preparations
- USEPA/OPP Pesticide Code 059803; Trade Names: Fennosan H 30, NCI-C55298, Tumex, USAF EK-794, Quinophenol.
... AVAILABLE IN USA IN TECHNICAL & REAGENT GRADES. IT IS ALSO AVAILABLE AS 0.5% SOLN (OR AEROSOL) SUITABLE FOR TOPICAL USE.
- 4.7 WGK Germany
- 3
- 4.7 RTECS
- VC4200000
- 4.7 Safety
-
Hazard Codes:
Xn
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 the label whenever 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
HS Code: 29334990
- 4.8 Specification
-
?8-Hydroxyquinoline (CAS NO.148-24-3) is a white to off-white or faintly yellow crystalline powder with phenolic odor.It is?insoluble in water. 8-Hydroxyquinoline darkens on exposure to light and readily forms stable metal chelates. It is incompatible with strong oxidizers and it is also incompatible with many metal ions.
It? is a monoprotic bidentate chelating agent. Related ligands are the Schiff bases derived from salicylaldehyde, such as salicylaldoxime and salen. In neutral solution, the hydroxyl is in the protonated form (pKa=9.89) and the nitrogen is not protonated (pKa=5.13).However, an excited-state zwitterionic isomer exists in which H+ is transfered from the oxygen (giving an oxygen anion) to the nitrogen (giving a protonated nitrogen cation).
- 4.9 Toxicity
- ORL-RAT LD50 1200 mg kg-1, ORL-MUS LD50 20000 mg kg-1, IPR-MUS LD50 43 mg kg-1, SCU-MUS LD50 84 mg kg-1, UNR-MAM LD50 1000 mg kg-1
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
148-24-3Total: 50 Synthesis Route
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Literatures:
Takacs, Attila; Szilagyi, Antal; Acs, Peter; Mark, Laszlo; Peixoto, Andreia F.; Pereira, Mariette M.; Kollar, Laszlo Tetrahedron, 2011 , vol. 67, # 13 p. 2402 - 2406
Yield: ~81%
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9. Other Information
- 9.0 Usage
- 8-Hydroxyquinoline is used as an antiseptic and disinfectant. Its alcoholic solution is used in liquid bandages. It is used to prepare tris(8-hydroxyquinolinato)aluminum, which finds application as a component of organic light-emitting diodes (OLED's). It is also used as a reagent and as a stabilizer of hydrogen peroxide in a rocket fuel oxidizer. It is used as a chelating agent and used as a carrier for radio-indium for diagnostic purposes. Its halogenated derivatives are used as anti-infective agents and oral antiamebics.
- 9.1 Merck
- 14,4843
- 9.2 BRN
- 114512
- 9.3 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).
- 9.4 Originator
- Chinosol,Chinosolfabrik
- 9.5 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).
- 9.6 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.
- 9.7 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).
- 9.8 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
- 9.9 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.
- 9.10 Therapeutic Function
- Antiseptic
- 9.11 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)
- 9.12 General Description
- White to off-white or faintly yellow crystalline powder. Phenolic odor.
- 9.13 Air & Water Reactions
- Insoluble in water.
- 9.14 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.
- 9.15 Hazard
- Toxic by ingestion. Questionable carcinogen.
- 9.16 Fire Hazard
- Flash point data for 8-Hydroxyquinoline are not available; however, 8-Hydroxyquinoline is probably combustible.
- 9.17 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.
- 9.18 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.
- 9.19 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.]
10. Computational chemical data
- Molecular Weight: 145.15798g/mol
- Molecular Formula: C9H7NO
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 145.052763847
- Monoisotopic Mass: 145.052763847
- Complexity: 138
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 33.1
- Heavy Atom Count: 11
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYByIAAAAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAACx8AAAHgAACAAADAzBngQ8xvIIEgCgAzRnRASCgCAxYiAI2CA/bJgKJuLSkZOEcAhkwBHY2AeQwLAOAAABAAACEAAAAAIAAAQgAAAAAAAAAA==
11. Question & Answer
-
Introduction 8-Hydroxyquinoline (8HQ) is a quinoline derivative that is utilized as a fungicide in agriculture and a preservative in the textile, wood, and paper industries. Known for its potent coor..
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8-hydroxyquinoline is a versatile raw material for synthesizing corrosion inhibitors. Research has shown that derivatives of 8-hydroxyquinoline can effectively inhibit corrosion on N80 steel in a hydr..
-
8-Hydroxyquinoline (8HQ), also known as 8-hydroxyquinoline, abbreviated as 8HQ, is an organic molecule with a wide range of applications in fields such as biomedical, materials science, and chemical a..
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Introduction 8-Hydroxyquinoline, also known as oxine or 8-quinolinol, is an organic compound with the molecular formula C9H7NO. It is a yellow solid that is soluble in organic solvents but has low sol..
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