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8-Hydroxyquinoline

  • 148-24-3
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Name 8-Hydroxyquinoline
Basic Information
Synonyms 8-hydroxy-quinolin;
8-OQ;
8-Oxyquinolin;
8-Quinol;
8-Quinolol;
CAS number 148-24-3
EINECS 205-711-1
Formula C9H7NO
Molecular Weight 145.16
Melting Point 70-73 °C(lit.)
Flashing Point 267°C
Water Solubility  INSOLUBLE
Boiling Point 267 °C752 mm Hg(lit.)
Density  1.0340
Storage temp Store at RT.
Refractive index  1.4500 (estimate)
Safety Information
Hazard Codes  Xn,Xi
Risk Statements 22-68-36/37/38
Safety Statements 45-36/37/39-26-36
RIDADR  2811
RTECS VC4200000
HazardClass 9
PackingGroup  III
HS Code  29334990
Description
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.
    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).