5-Nitroquinoline Chemical Properties

Melting point:

71-73 °C (lit.)

Boiling point:

70-73°C

Density 

1.2190 (estimate)

refractive index 

1.6820 (rough estimate)

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Slightly soluble in water

form 

powder to crystal

pka

2.80±0.12(Predicted)

color 

Plates from EtOH (aq)

InChI

InChI=1S/C9H6N2O2/c12-11(13)9-5-1-4-8-7(9)3-2-6-10-8/h1-6H

InChIKey

NDDZXHOCOKCNBM-UHFFFAOYSA-N

SMILES

N1C2C(=C([N+]([O-])=O)C=CC=2)C=CC=1

CAS DataBase Reference

607-34-1(CAS DataBase Reference)

NIST Chemistry Reference

Quinoline, 5-nitro-(607-34-1)

EPA Substance Registry System

5-Nitroquinoline (607-34-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-40-68-36/37/38

Safety Statements 

7-22-36-45-36/37/39-26

WGK Germany 

3

RTECS 

VC1850000

Hazard Note 

Irritant

HS Code 

29334900

Toxicity

mmo-sat 10 mg/plate MUREAV 92,29,82

MSDS

• Language:English Provider:5-Nitroquinoline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Nitroquinoline Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx. Seealso other nitroquinoline entries.

Synthesis

General procedure for the synthesis of 8-nitroquinoline and 5-nitroquinoline from quinoline: Pure sulfuric acid (H2SO4) was slowly added to 1 equivalent of quinoline at 0 °C. Subsequently, 3 equivalents of 65% nitric acid (HNO3) were added dropwise and the reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was poured sequentially into ice water, neutralized with sodium carbonate (Na2CO3) to pH neutral, and then extracted twice with dichloromethane (DCM). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate (Na2SO4) and finally the solvent was evaporated under vacuum. 8-Nitroquinoline (compound 35) was obtained as a light yellow solid in 34% yield; melting point 90 °C, literature value: 89-90 °C [43].1H NMR (200 MHz, CDCl3) δ: 7.53-7.66 (m, 2H), 8.04 (d, J = 8.0 Hz, 2H), 8.27 (dd, J = 1.6 and 8.4 Hz, 1H). 9.70 (dd, J = 1.7 and 4.2 Hz, 1H). 13C NMR (50 MHz, CDCl3) δ: 122.8 (CH), 123.8 (CH), 125.3 (CH), 129.0 (C), 132.0 (CH), 136.1 (CH), 139.5 (C), 148.2 (C), 152.6 (CH ). Recrystallization by isopropanol afforded 5-nitroquinoline (compound 36) as a light yellow solid in 38% yield; melting point 71 °C, literature value: 71-72 °C [41].1H NMR (200 MHz, CDCl3) δ: 7.61-7.68 (m, 1H), 7.76-7.85 (m, 1H), 8.36-8.45 (m, 2H). 8.98-9.04 (m, 2H).13C NMR (50MHz, CDCl3) δ: 121.2 (C), 123.9 (CH), 124.6 (CH), 127.5 (CH), 131.9 (CH), 136.6 (CH), 145.5 (C), 148.2 (C), 151.6 (C).

Purification Methods

Crystallise 5-nitroquinoline from pentane, then from *benzene. The hydrochloride has m 224o and the picrate has m 206o, 214o(from MeOH). [Beilstein 20 H 371, 20 II 235, 20 III/IV 3397.]

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 75 - 86
[2] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 135 - 152
[3] Journal of the Chemical Society, 1892, vol. 61, p. 788
[4] Chemische Berichte, 1885, vol. 18, p. 1243
[5] Journal fuer Praktische Chemie (Leipzig), 1896, vol. <2> 53, p. 392

5-Nitroquinoline(607-34-1)Related Product Information

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