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Merck
CN

55067

6-Quinolinol

technical, ≥95% (HPLC)

Synonym(s):

6-Hydroxyquinoline

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
Molecular Weight:
145.16
EC Number:
209-454-6
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
113196
MDL number:
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grade

technical

assay

≥95% (HPLC)

mp

188-190 °C (lit.), 192-196 °C

SMILES string

Oc1ccc2ncccc2c1

InChI

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

InChI key

OVYWMEWYEJLIER-UHFFFAOYSA-N

General description

6-Quinolinol can be prepared by refluxing a mixture of 6-methoxyquinoline bisulfate and concentrated hydrobromic acid followed by neutralization with ammonia.

Application

6-Quinolinol may be used in the preparation of the following heterocyclic compounds:
  • 1,2-dihydro-1-aryl[1,3]oxazino[5,6-f]quinolin-3-ones
  • highly substituted 4H-chromene derivatives
  • dioxino(5,4-f)quinoline
  • methyl 3-oxo-3H-pyrano[3,2-f]quinoline-1-carboxylate

Regulatory Information

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Synthesis of novel pyridocoumarins and benzo-fused 6-azacoumarins.
Galariniotou E, et al.
Tetrahedron, 63(34), 8298-8304 (2007)
A clean synthesis of oxazino [5,6-f] quinolinone and naphtho [1,2-e] oxazinone derivatives.
Mosslemin MH, et al.
Monatshefte fur Chemie / Chemical Monthly, 139(10), 1247-1250 (2008)
A three-component, one-pot synthesis of oxazinoquinolin-3-one derivatives.
Shakibaei GI, et al.
Journal of Heterocyclic Chemistry, 45(5), 1481-1484 (2008)
G Bott et al.
Biological chemistry Hoppe-Seyler, 372(6), 381-383 (1991-06-01)
Two strains, using 6-hydroxyquinoline as sole source of energy, carbon and nitrogen, have been isolated. These bacteria, designated 31/1 Fa1 and 31/2 A1, are also able to degrade quinoline. According to their physiological properties strain 31/1 Fa1 has been identified
Richard B Greenwald et al.
Bioorganic & medicinal chemistry letters, 13(3), 577-580 (2003-02-05)
Selective acylation of the phenolic hydroxyl group of 10-hydroxycamptothecin has been accomplished using phenyl dichlorophosphate. Additional modification of the 10-OH as an ether permits a 20-acyl derivative to be synthesized. This result along with data from a 6-hydroxyquinoline model strongly

Global Trade Item Number

SKUGTIN
M104-25MG04061832091792
M104-5MG04061832091808

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