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304484

Sigma-Aldrich

6-Hydroxyquinoline

95%

Synonym(s):

6-Quinolinol, 6-Hydroxyquinoline

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
Molecular Weight:
145.16
Beilstein:
113196
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

mp

188-190 °C (lit.)

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

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General description

6-Hydroxyquinoline is an ideal photoacid system for exploring excited-state proton transfer (ESPT) reactions. The excited-state proton transfer and geminate recombination of 6-hydroxyquinoline encaged in catalytic Na+-exchanged faujasite zeolites X and Y have been explored by measuring steady-state and picosecond time-resolved spectra.

Application

6-Hydroxyquinoline was used in synthesis of 2,6-substituted-benzo[d]thiazole analogs and 2,4-substituted-benzo[d]thiazole analogs.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yu-Hui Liu et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 128, 280-284 (2014-04-01)
6-Hydroxyquinoline (6HQ) is an ideal photoacid system for exploring excited-state proton transfer (ESPT) reactions. We have previously (Mahata et al. (2002)) shown that the ESPT reaction between 6HQ and trimethylamine (TMA) leads to an "unusual" emission in the 440-450 nm
Katharigatta Narayanaswamy Venugopala et al.
European journal of medicinal chemistry, 65, 295-303 (2013-06-04)
A novel and efficient one pot synthesis was developed for 2,6-substituted-benzo[d]thiazole analogues 4a-k and 2,4-substituted-benzo[d]thiazole analogues 4l-pvia three component condensation reaction of substituted arylaldehyde, 2-amino-6-halo/4-methyl-benzo[d]thiazole and 2-naphthol or 6-hydroxyquinoline in presence of 10% w/v NaCl in water by microwave method.
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
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
M S Mehata et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 59(3), 559-567 (2003-01-14)
Fluorescence characteristics of 6-hydroxyquinoline (6-HQ) have been studied at room temperature in Nafion(R) film by steady state and nano-second time-resolved fluorescence spectroscopy. The fluorescence spectrum exhibits single emission band corresponding to the protonated form of 6-HQ in this matrix. However

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