| Identification | More | [Name]
8-Nitroquinoline | [CAS]
607-35-2 | [Synonyms]
8-NITROQUINOLINE
AKOS 214-03
8-nitro-quinolin
Quinoline, 8-nitro-
Quinoline,8-nitro-
8-Nitroqunioline
8-Nitroquinoline,98%
8-Nitrochinolin
NSC 346 | [EINECS(EC#)]
210-135-9 | [Molecular Formula]
C9H6N2O2 | [MDL Number]
MFCD00006806 | [Molecular Weight]
174.16 | [MOL File]
607-35-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [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]
607-35-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect.
R68:Possible risk of irreversible effects. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [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 Information | Back Directory | [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 |
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