8-Quinolinol

8-Quinolinol - Names and Identifiers

Name	8-Hydroxyquinoline
Synonyms	HQ OQ 8-OQ OXIN Tumex Oxine Fennosan 8-Quinol fennosan 8-Quinolol quinophenol fennosanh30 oxychinolin 8-Quinolinol oxyquinoline phenopyridine Chinolin-8-ol 8-Oxyquinolin Fennosan H 30 Quinolin-8-ol 8-oxyquinoline Quinoleine-8-ol Hydroxychinolin oxybenzopyridine Hydroxyquinoline 8-Hydroxyquinoline 8-hydroxy-quinolin Azanaphthalene-8-ol Hydroxy-8-Quinoline hydroxybenzopyridine
CAS	148-24-3
EINECS	205-711-1
InChI	InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
InChIKey	MCJGNVYPOGVAJF-UHFFFAOYSA-N

8-Quinolinol - Physico-chemical Properties

Molecular Formula	C9H7NO
Molar Mass	145.16
Density	1.0340
Melting Point	70-73°C(lit.)
Boling Point	267°C752mm Hg(lit.)
Flash Point	267°C
Water Solubility	INSOLUBLE
Solubility	Easily soluble in ethanol, acetone, chloroform, benzene and mineral acid, almost insoluble in water
Vapor Presure	0.221Pa at 25℃
Appearance	White or light yellow crystal or crystalline powder
Color	White to pale yellow or light beige
Merck	14,4843
BRN	114512
pKa	5.017(at 20℃)
Storage Condition	Store below +30°C.
Sensitive	Light Sensitive
Refractive Index	1.4500 (estimate)
MDL	MFCD00006807
Physical and Chemical Properties	White needle-like crystals. The melting point of 76 deg C, boiling point of 266.6 deg C (100.3kPa). Soluble in ethanol, benzene, chloroform, acetone and dilute acid, insoluble in water.
Use	The product is an intermediate of halogenated quinoline anti-amoeba drugs, including quiniodoform, chloroiodoquinoline, diiodoquinoline, etc. These drugs play an anti-amoebic effect by inhibiting intestinal commensal bacteria, are effective for amoebic dysentery, and have no effect on extraintestinal amoebic protozoa. In recent years, foreign reports of this class of drugs can cause subacute spinal optic neuropathy, so the drug has been banned in Japan and the United States?

8-Quinolinol - Risk and Safety

Risk Codes	R22 - Harmful if swallowed R68 - Possible risk of irreversible effects R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	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.
UN IDs	2811
WGK Germany	3
RTECS	VC4200000
TSCA	Yes
HS Code	29334990
Hazard Note	Harmful/Irritant
Hazard Class	9
Packing Group	III
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).

8-Quinolinol - Nature

Open Data Verified Data

white or light yellow crystal or crystalline powder, light black, a smell of carbonic acid. Melting point 76 °c. The boiling point is about 267 °c. Soluble in alcohol, acetone, chloroform, benzene, almost insoluble in water.

Last Update：2024-01-02 23:10:35

8-Quinolinol - Preparation Method

Open Data Verified Data

O-aminophenol, O-nitrophenol, glycerol, and glacial acetic acid were mixed, concentrated sulfuric acid was added in portions, and the mixture was heated until boiling began. Unreacted O-nitrophenol was then removed by steam distillation at reflux on an oil bath. After cooling, neutralization with sodium hydroxide solution and recovery by steam distillation, 8-Hydroxyquinoline was obtained.

Last Update：2022-01-01 09:27:21

8-Quinolinol - Use

Open Data Verified Data

as a complexing agent and extractant for precipitation and separation of metal ions, it can complex with Cu2, Be2, Mg2, Caz, Sr2, Ga3, In3 and other metal ions. Standard for the determination of heterocyclic nitrogen by organic microanalysis, organic synthesis. It is also an intermediate of dyes, pesticides and halogenated quinoline anti-amoeba drugs. Its sulfate and copper salts are excellent preservatives.

Last Update：2022-01-01 09:27:21

8-Quinolinol - Safety

Open Data Verified Data

mice were injected intraperitoneally with LD50:48mg/kg.

Last Update：2022-01-01 09:27:22

8-Quinolinol - Reference Information

LogP	1.85 at 25℃
(IARC) carcinogen classification	3 (Vol. 13, Sup 7) 1987
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
use	this product is an intermediate of halogenated quinoline anti-amoebic drugs, including quinodoform, chloroiodoquinoline, diiodoquinoline, etc. These drugs play an anti-amoebic effect by inhibiting intestinal symbiotic bacteria, are effective for amoebic dysentery, and have no effect on intestinal amoeba protozoa. In recent years, it has been reported abroad that this class of drugs can cause subacute spinal optic neuropathy, so this drug has been banned in Japan and the United States. Diiodoquinoline is less common than chloroiodoquinoline. 8-Hydroxyquinoline is also an intermediate of dyes and pesticides. Its sulfate and copper salts are excellent preservatives, disinfectants and antifungal agents. This product is a complexometric titration indicator for chemical analysis. Used as a reagent for the determination of bismuth, magnesium, copper, zinc and organic element nitrogen; used as a pharmaceutical intermediate, it is a raw material for the synthesis of Kexilining, chloroiodoquinoline, and wheezing sensitivity. It is also a dye and pesticide Intermediate, extractant. Pharmaceutical intermediates; Pesticide and dye intermediates The precipitant and extractant for precipitating and separating metal ions can be complexed with the following metal ions: cu 2, Be 2, Mg 2, Ca 2, Sr 2, Ba 2, Zn 2, Cd 2, Al 3, Ga 3, In 3, Tl 3, Yt 3, La 3, Pb 2, B 3, Sb 3, Cr 3, MoO 22, Mn 2, Fe 3, Co 2, Ni 2, Pd 2, Ce 3. used in manufacturing dyes, pesticides and pharmaceutical intermediates; used as complexing indicators and chromatography reagents; also can be used as RNA synthesis inhibitors, and have bactericidal inhibitory effects on Trichoderma vulgaris (Trichophyton mentagrophytes), Myrothecium verrucaria) and Trichoderma viride (Trichoderma viride)
Production method	Made from o-aminophenol by cyclize reaction. Glycerol is added into the acid-resistant reaction pot, concentrated sulfuric acid is slowly added under stirring, o-aminophenol and o-nitrophenol are added in sequence, and 65% of the total amount of fuming sulfuric acid is added first. Heating to 125 ℃, stop heating, naturally raise to 140 ℃, and wait for the temperature to drop back to 136 ℃. Continue to add the remaining fuming sulfuric acid and keep the temperature at 137 ℃. After adding acid, keep the temperature for 4 hours, cool to below 100 ℃, draw into an acid-resistant pot containing 10 times the amount of water (calculated by o-aminophenol), stir, heat to 75-80 ℃, and neutralize with 30% sodium hydroxide solution to a pH of 7-7.2. Release the precipitate while it is hot, cool it into a block, and sublimate under reduced pressure to obtain a finished product of 8-hydroxyquinoline.
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)

Last Update：2024-04-09 02:00:07

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