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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

Quality Level

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
Anna Michta et al.
Acta crystallographica. Section C, Crystal structure communications, 65(Pt 2), o66-o69 (2009-02-05)
The title compound, C(9)H(7)NO, has two symmetry-independent molecules in the asymmetric unit, which have different conformations of the hydroxy group with respect to the quinoline ring. One of the molecules adopts a cis conformation, while the other shows a trans

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