1 Basic information
Chinese Name: 8 – hydroxyquinoline
Chinese alias: 8 – quinoline hydroxide 8 – hydroxy naphthalene nitrogen, ortho hydroxy nitrogen (Miscellaneous) naphthalene, oxine , 8 – hydroxy-naphthyridine
Name :8-Hydroxyquinoline
English Name :8-Hydroxyquinoline; 8-Oxychinolin; 8-Quinolinol; Oxine
Grade: AR
CAS Number :148 -24-3
Formula: C9H7NO
Molecular Weight: 145.16
CAS Number :148 -24-3
No. MDL: MFCD00006807
EINECS No. :205 -711-1
RTECS Number: VC4200000
BRN No.: 114512
PubChem number: 24855220
2 Characters
White or light yellow crystal or crystalline powder , insoluble in water and ether , soluble in ethanol , acetone, chloroform , benzene or dilute acid, can be sublimated. Less corrosive. Low toxicity, LD504800mg/kg.
3 Quality Standards
|
Name (content and impurity content%) |
Index |
Result |
|
8 – hydroxy quinoline (C9H7NO) content ≥ |
99.5 |
99.7 |
|
Melting point ℃ |
73.0 ~ 74.5 (1 ℃) |
73.1 ~ 74.0 (1 ℃) |
|
Sensitivity tests for magnesium |
Qualified |
Qualified |
|
Acid dissolution test |
Qualified |
Qualified |
|
Residue on ignition (as sulfate) ≤ |
0.02 |
0.015 |
|
Chloride (Cl) ≤ |
0.002 |
0.0015 |
|
Sulfate (SO4) |
0.01 |
0.006 |
4 Physical Parameters
[1]
Melting point (º C): 75 ~ 76
Boiling Point (º C): 267
Density: 1.03
5 Quality Specifications
Purity: ≥ 99%
Melting point ≥ 75 ℃
Residue on ignition (as sulfate): ≤ 0.02%
Chloride : ≤ 0.002%
Sulfate: ≤ 0.01%
Magnesium sensitivity test: pass
Acid dissolution test: pass
6 dissolved
Soluble in ethanol , acetone, chloroform , benzene, and a mineral acid, almost insoluble in water .
8 – hydroxy quinoline is bisexual, soluble in strong acid , alkali, alkali ions in ionization, can be combined in acid hydrogen ions in PH = 7时solubility minimum.
7 toxicological data
1 Acute toxicity: rat oral LD50: 1200 mg / kg; mouse oral LC50: 20 gm / kg;
Intraperitoneal LD rat: 43 gm / kg; mouse subcutaneous LCLo: 83600 ug / kg.
2 inhalation toxicity: rat:> 1210 mg/m3/6H
The substance may be hazardous to the environment, the water should be given special attention.
8 molecular structure data
1, the molar refractive index: 44.06
2, molar volume (m3/mol): 115.2
3, parachor (90.2K): 320.2
4, the surface tension (dyne / cm): 59.7
5, the polarization rate (10-24cm3): 17.47
9 computational chemistry data
A hydrophobic parameter calculation reference value (XlogP): 2
2, the number of hydrogen bonds for the body: 1
3, the number of hydrogen bond acceptors: 2
4, rotatable bond: 0
5, topological molecular polar surface area (TPSA): 33.1
6, the number of heavy atoms: 11
7, the surface charge: 0
8, the complexity: 138
9, the number of atomic isotopes: 0
10, determines the number of atoms stereocenter: 0
11, the number of uncertain atom stereocenter: 0
12, determines the number of bond stereocenter: 0
13, the number of uncertain bond stereocenter: 0
14, the number of covalent bond unit: 1
10 synthetic
1 o-aminophenol by cyclization reaction. Glycerol was added to the acid reaction pot, stirring slowly adding concentrated sulfuric acid, while the o-aminophenol , o-nitrophenol were added sequentially, fuming sulfuric acid to join the 65% of the total. Heating up to 125 ℃, heating was stopped and warm naturally to 140 ℃, when the temperature was returned to 136 ℃. The rest continues oleum added maintaining the temperature at 137 ℃. After the addition of acid, heat 4h, cooling to 100 ℃, 10 times the amount of pumped water bloom (in o-phenol) acid pot was stirred and heated to 75-80 ℃, with 30% sodium hydroxide solution to a pH of 7-7.2. The precipitate was discharged hot, cooling blocks, sublimation under reduced pressure, to give 8 – hydroxyquinoline products.
2 o-aminophenol, o-nitrophenol, glycerol , acetic acid mixture of concentrated sulfuric acid was added, and the mixture was heated to boiling until the beginning. And then refluxed on an oil bath to remove unreacted nitrophenol by steam distillation. Cooled, neutralized with sodium hydroxide solution and recovered by steam distillation, i.e., to give 8 – hydroxyquinoline.
3 of quinoline sulfonated get 8 – quinoline sulfonic acid groups, and then after alkali fusion get 8 – hydroxy quinoline bases, and finally by acidification to give 8 – hydroxy quinoline. Preparation process is as follows:
① sulfonation quinoline as raw materials in the raw material was added slowly with stirring to sulfuric acid in a sand bath heated at 100 ~ 180 ℃, sulfonated 2 ~ 3h. Then cooled to room temperature, then further cooled ice, filtered dried to give product 8 – quinoline sulfonic acid.
② alkali melt process under stirring, the sulfonated product was added slowly to the molten base, in the melt of about 200 ~ 240 ℃ 30 ~ 40min, cooled water was added and heated to dissolve all the cooling to room temperature After acid and then neutralized to pH = 7, upon crystallization, filtration, the filter cake was dry.
③ The alkali fusion product distillation process using steam distillation, cooling and crystallization is the product 8 – hydroxy quinoline.
11 The main purpose
1, is widely used for the determination and separation of metals. Precipitating agent and precipitation and separation of metal ions in the extraction agent, 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
1 used as pharmaceutical intermediates, synthetic grams Xie Li Ning, clioquinol, flutter respite sensitive materials, but also dye, pesticide intermediates. The product is a halogenated quinoline class of anti-amoebic drug intermediates, including quinoline iodoform, clioquinol, iodoquinol so on. These drugs inhibit the intestinal commensal bacteria play a role in anti-amoebic of amoebic dysentery effective, no outside influence on intestinal amoeba. Foreign reports this class of drugs can cause subacute optic neuropathy, the drug has been disabled in Japan and the United States, caused by the disease iodoquinol than clioquinol rare. 8 – hydroxy quinoline also dye, pesticide intermediates. Copper sulfate and is an excellent antiseptic, disinfectant and fungicide. The product is a complex indicator for chemical analysis.
2 is used as a complexing agent and an extractant precipitation and separation of metal ions, with 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, and other metal ions. Determination of organic trace analysis of nitrogen heterocyclic organic synthesis. Also dyes, pesticides and halogenated quinoline class of anti-amoebic drug intermediates. Copper sulfate and is an excellent antiseptic .
3 of epoxy adhesive can be added to improve the metal (especially stainless steel) adhesive strength and heat aging resistance, the amount is generally 0.5 to 3 parts. Halogenated quinoline class of anti-amebic drugs intermediates, pesticide, dye intermediates. Complexometric titration can be used as an antifungal agent, a preservative and industrial polyester resin, phenol resin, and a hydrogen peroxide stabilizer, or a chemical analysis indicator .
(4) The product is an intermediate halogenated quinoline drugs, but also dyes, pesticide intermediates. Copper sulfate and is an excellent antiseptic, disinfectant and fungicide. Cosmetics maximum allowable content (mass fraction) was 0.3%, sunscreen products and products for children under 3 years of age (as talcum powder) is disabled and should indicate on the product label “disabled children under 3 years of age.” In dealing with bacterial infections and bacterial infections of the skin, eczema, lotion 8 – hydroxy quinoline mass fraction of 0.001% to 0.02%. It is also used as a disinfectant, antiseptic and fungicide, and its strong anti-fungal effect. 8 – hydroxyquinoline sulfate used in skin creams and lotions content (mass fraction) of 0.05% to 0.5%.
12 Risk Phrases
R22 Harmful if swallowed.
R37 Irritating to respiratory system.
R38 irritating to the skin. [2]
13 storage transport
Dark dry and ventilated place
14 Hazard statement
Dangerous code: Xn
Dangerous Level: 22