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Sigma-Aldrich

8-Hydroxy-5-nitroquinoline

96%

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Synonym(s):
5-Nitro-8-quinolinol
Empirical Formula (Hill Notation):
C9H6N2O3
CAS Number:
4008-48-4
Molecular Weight:
190.16
EC Number:
223-662-4
MDL number:
MFCD00006791
UNSPSC Code:
12352100
PubChem Substance ID:
24848465
NACRES:
NA.22

Quality Level

100

Assay

96%

form

powder

mp

181-183 °C (lit.)

solubility

alcohol: very slightly soluble
diethyl ether: very slightly soluble
hydrochloric acid: freely soluble (hot)

SMILES string

Oc1ccc([N+]([O-])=O)c2cccnc12

InChI

1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H

InChI key

RJIWZDNTCBHXAL-UHFFFAOYSA-N

Related Categories

Application

8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents.

Biochem/physiol Actions

8-Hydroxy-5-nitroquinoline is an effective anti-microbial and anti-cancer agent. It is an effective drug for the treatment of urinary tract infections due to gram negative bacilli.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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Serena Veschi et al.
Journal of experimental & clinical cancer research : CR, 37(1), 236-236 (2018-09-23)
Pancreatic cancer (PC) is the fourth most common cause of cancer death. Combination therapies with classical chemotherapeutic agents improved treatment of advanced PC at the cost of a relevant toxicity, but the 5-year survival rate remains below 5%. Consequently, new
Highly CO2-soluble 5-Amido-8-hydroxyquinoline Chelating Agents for Extraction of Metals in Sc-CO2.
Chang F, et al.
Bull. Korean Chem. Soc., 29(7), 1327-1327 (2008)
C Pelletier et al.
Antimicrobial agents and chemotherapy, 39(3), 707-713 (1995-03-01)
The antibacterial activity of nitroxoline (NIT), an antibiotic used in the treatment of acute or recurrent urinary tract infections caused by Escherichia coli, is decreased in the presence of Mg2+ and Mn2+ but not Ca2+. In order to elucidate the
A V Yatsenko et al.
Acta crystallographica. Section C, Crystal structure communications, 58(Pt 1), o19-o21 (2002-01-10)
The crystal structures of 8-hydroxy-5-nitroquinoline, C9H6N2O3, (I), and 8-hydroxy-5-nitroquinolinium chloride, C9H7N2O3+*Cl-, (II), have been determined from X-ray powder data. In (I), the molecules are linked via moderately strong hydrogen bonds to form dimers. Such a packing motif is likely to
Mohamed M Ghoneim et al.
Bioelectrochemistry (Amsterdam, Netherlands), 80(2), 162-168 (2010-09-14)
Nitroxoline has been reduced at the mercury electrode in buffered solutions (pH 2-11) in two irreversible cathodic steps. The first step was attributed to reduction of -NO(2) group to the hydroxylamine stage and the second one to reduction-saturation of the
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