| Identification | More | [Name]
4-Chloro-3-nitroquinoline | [CAS]
39061-97-7 | [Synonyms]
4-CHLORO-3-NITROQUINOLINE
QUINOLINE, 4-CHLORO-3-NITRO-
4-Chloro-3-nitroquinoline ,98% | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C9H5ClN2O2 | [MDL Number]
MFCD07369246 | [Molecular Weight]
208.6 | [MOL File]
39061-97-7.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystal powder | [Melting point ]
121-122°C | [Boiling point ]
333.8±22.0 °C(Predicted) | [density ]
1.484±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-0.28±0.24(Predicted) | [color ]
Pale Yellow | [Detection Methods]
HPLC,NMR,MS | [InChI]
InChI=1S/C9H5ClN2O2/c10-9-6-3-1-2-4-7(6)11-5-8(9)12(13)14/h1-5H | [InChIKey]
ZRFUZDDJSQVQBY-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C(Cl)=C([N+]([O-])=O)C=1 | [CAS DataBase Reference]
39061-97-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystal powder | [Uses]
4-Chloro-3-nitroquinoline (cas# 39061-97-7) is a compound useful in organic synthesis. | [Synthesis]
General procedure for the synthesis of 4-chloro-3-nitroquinoline from 4-hydroxy-3-nitroquinoline: The intermediate 3-nitro-4-hydroxyquinoline (18.7 g, 98.4 mmol) was suspended in dichloromethane (150 mL). Thionyl chloride (17.2 mL, 236 mmol) and N,N-dimethylformamide (DMF, 9.2 mL, 118 mmol) were added sequentially to the suspension. The reaction mixture was heated to reflux and kept reacting overnight. Upon completion of the reaction, the mixture was slowly poured into ice water. The organic and aqueous layers were separated and the organic layer was washed sequentially with saturated sodium bicarbonate solution, water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue (20.52 g, 93% yield) can be used directly in the subsequent reaction without further purification. | [References]
[1] Patent: EP2674170, 2013, A1. Location in patent: Paragraph 0228
[2] Patent: US2014/141033, 2014, A1. Location in patent: Page/Page column
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1202 - 1206
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 11, p. 3354 - 3361
[5] Patent: WO2007/89507, 2007, A1. Location in patent: Page/Page column 20-21 |
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