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32502

Sigma-Aldrich

8-Quinolinol

puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99% (perchloric acid titration)

Synonym(s):

8-Hydroxyquinoline, 8-Oxychinolin, Oxine

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
148-24-3
Molecular Weight:
145.16
Beilstein:
114512
EC Number:
205-711-1
MDL number:
MFCD00006807
UNSPSC Code:
12352100
PubChem Substance ID:
57648688
NACRES:
NA.21

grade

ACS reagent
puriss. p.a.

Quality Level

200

Agency

reag. Ph. Eur.

Assay

≥99% (perchloric acid titration)

form

solid

technique(s)

titration: suitable

impurities

≤0.05% insoluble in ethanol

ign. residue

≤0.05% (as SO4)

mp

72.5-74.0 °C
72.5-75 °C

anion traces

chloride (Cl-): ≤10 mg/kg
sulfate (SO42-): ≤100 mg/kg

suitability

passes test for suitability for Mg decision

antibiotic activity spectrum

fungi

Mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

Oc1cccc2cccnc12

InChI

1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

InChI key

MCJGNVYPOGVAJF-UHFFFAOYSA-N

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General description

8-Quinolinol (QOH) forms complexes with heavy metals [Pt(II), Pb(II), Bi(III), Ir(III)]. These complexes show long-lived phosphorescence and excited state absorption in solutions. It has been reported to form metal chelate complexes. Immobilized 8-quinolinol has been widely used in the preconcentration step during the extraction of metals.
Chemical structure: quinolone

Signal Word

Danger

Hazard Statements

H301,H317,H318,H360D,H410

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Repr. 1B - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD9368
BCCC2732
BCCC1726
BCCC1878
BCCC0360

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Phosphorescent 8-quinolinol metal chelates. Excited-state properties and redox behavior.
Ballardini R, et al.
Inorganic Chemistry, 25(22), 3858-3865 (1986)
Synthesis of silica-immobilized 8-quinolinol with (aminophenyl) trimethoxysilane.
Marshall MA and Mottola HA.
Analytical Chemistry, 55(13), 2089-2093 (1983)
The reactions of 8-quinolinol.
Phillips JP.
Chemical Reviews, 56(2), 271-297 (1956)
Synthesis, crystal structure and spectral properties of VO (acetylacetone benzoylhydrazone)(8-quinolinol).
Liu SX and Gao S.
Polyhedron, 17(1), 81-84 (1998)
María Isabel Fernández-Bachiller et al.
Journal of medicinal chemistry, 53(13), 4927-4937 (2010-06-16)
Tacrine and PBT2 (an 8-hydroxyquinoline derivative) are well-known drugs that inhibit cholinesterases and decrease beta-amyloid (Abeta) levels by complexation of redox-active metals, respectively. In this work, novel tacrine-8-hydroxyquinoline hybrids have been designed, synthesized, and evaluated as potential multifunctional drugs for
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