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Basic Information
CAS No.: 4008-48-4
Name: Nitroxoline
Article Data: 29
Molecular Structure:
Molecular Structure of 4008-48-4 (Nitroxoline)
Formula: C9H6N2O3
Molecular Weight: 190.158
Synonyms: 5-(Hydroxyl[oxido]amino)-8-hydroxyquinoline;5-Nitro-8-hydroxyquinoline;5-Nitro-8-oxychinoline;5-Nitro-8-oxyquinoline;5-Nitro-8-quinolinol;5-Nitrox;5-Nitroxine;5NOK;8-Hydroxy-5-nitroquinoline;BAS 58;NSC 74947;NSC 74948;Nibiol;Nitroxolin;Noxibiol;
EINECS: 223-662-4
Density: 1.496 g/cm3
Melting Point: 181-183 °C(lit.)
Boiling Point: 419 °C at 760 mmHg
Flash Point: 207.2 °C
Appearance: ochre-yellow to brownish crystalline powder
Hazard Symbols: ToxicT, IrritantXi, HarmfulXn
Risk Codes: 23/24/25-36/37/38-22/24/25-20/21/22
Safety: 26-36-45
Transport Information: UN 2811 6.1/PG 3
PSA: 78.94000
LogP: 2.37180
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Specification

The IUPAC name of 5-Nitro-8-hydroxyquinoline is 5-nitroquinolin-8-ol. With thw CAS registry number 4008-48-4, it is also named as 8-Hydroxy-5-nitroquinoline;  Nitroxoline. The product's categories are quinoline & isoquinoline, quinolines, hydroxyquinolines, nitroquinolines and pesticide intermediates. It is ochre-yellow to brownish crystalline powder which is used as pharmaceutical intermediates and antibiotic. This chemical is stable under normal temperatures and pressures. It is incompatibilities with strong oxidizing agents and strong bases.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.54; (4)ACD/LogD (pH 7.4): -0.08; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.04; (8)ACD/KOC (pH 7.4): 2.4; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.728; (13)Molar Refractivity: 50.61 cm3; (14)Molar Volume: 127 cm3; (15)Polarizability: 20.06×10-24 cm3; (16)Surface Tension: 76.5 dyne/cm; (17)Enthalpy of Vaporization: 69.87 kJ/mol; (18)Vapour Pressure: 1.29E-07 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 190.037842; (21)MonoIsotopic Mass: 190.037842; (22)Topological Polar Surface Area: 78.9; (23)Heavy Atom Count: 14

Preparation of 5-Nitro-8-hydroxyquinoline: It can be obtained by quinolin-8-ol. The reaction type is nitration. This reaction needs reagent Cu(NO3)2 and solvent acetic acid and H2O at microwave irradiation. The reaction time is 30 s. The yield is 70%.

Uses of 5-Nitro-8-hydroxyquinoline: It can react with morpholine and formaldehyde to get 7-morpholinomethyl-5-nitro-quinolin-8-ol. This reaction needs reagent pyridine and solvent H2O at temperature of 50-60 °C. The reaction time is 40 min. The yield is 84%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. Smiles: c12c(c(ccc1[N+](=O)[O-])O)nccc2;
2. InChI: InChI=1/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H.

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 8300ug/kg (8.3mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archiv fuer Toxikologie. Vol. 20, Pg. 313, 1965.
mouse LD50 oral 104mg/kg (104mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archiv fuer Toxikologie. Vol. 20, Pg. 313, 1965.
rat LD50 oral 510mg/kg (510mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archiv fuer Toxikologie. Vol. 20, Pg. 313, 1965.