8-Nitroquinoline

8-Nitroquinoline Property

Melting point:

89-91 °C (lit.)

Boiling point:

305.12°C (rough estimate)

Density 

1.2190 (estimate)

refractive index 

1.6820 (rough estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

1.20±0.17(Predicted)

color 

Monoclinic crystals from alcohol

Water Solubility 

Soluble in ethanol, ethyl ether and benzene, slightly soluble in cold water.

BRN 

135178

InChI

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

InChIKey

OQHHSGRZCKGLCY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

607-35-2(CAS DataBase Reference)

NIST Chemistry Reference

8-Nitro quinoline(607-35-2)

EPA Substance Registry System

Quinoline, 8-nitro- (607-35-2)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

26-27-36/37/39-36

WGK Germany 

3

RTECS 

VC1925000

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HS Code 

29334900

Hazardous Substances Data

607-35-2(Hazardous Substances Data)

Toxicity

TD orl-rat: 36,400 mg/kg/2Y-C:CAR,REP CALEDQ14,115,81

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H351Suspected of causing cancer

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

8-Nitroquinoline Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powder

Uses

8-Nitroquinoline was used to prepare furazano [3,4-h] quinoline. It was also used to synthesize corresponding 2-substituted phenoxy-6-methoxy-8-aminoquinoline.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

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 water, neutralized with sodium carbonate (Na2CO3) and then extracted twice with dichloromethane. The organic layer was washed with water and dried with anhydrous sodium sulfate (Na2SO4) followed by evaporation of the solvent 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).

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