| Identification | Back Directory | [Name]
4-CHLORO-6-NITROQUINAZOLINE | [CAS]
19815-16-8 | [Synonyms]
4-choro-6-nitroquinazoline
4-Chloro-6-nitro-quizoline
4-CHLORO-6-NITROQUINAZOLINE
Quinazoline,4-chloro-6-nitro- | [Molecular Formula]
C8H4ClN3O2 | [MDL Number]
MFCD00464269 | [MOL File]
19815-16-8.mol | [Molecular Weight]
209.59 |
| Chemical Properties | Back Directory | [Melting point ]
128 °C | [Boiling point ]
380.0±22.0 °C(Predicted) | [density ]
1.566±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Dichloromethane | [form ]
Solid | [pka]
0.14±0.50(Predicted) | [color ]
Brown | [CAS DataBase Reference]
19815-16-8 |
| Hazard Information | Back Directory | [Chemical Properties]
Brown Solid | [Uses]
Intermediate in the preparation of anticancer agents and enzyme inhibitors. | [Synthesis]
Step 1: Synthesis of 4-chloro-6-nitroquinazoline
To a solution of toluene (200 mL) containing 6-nitroquinazolin-4-ol (9.00 g, 47.1 mmol) and triethylamine (TEA, 9.53 g, 94.2 mmol) was slowly added phosphorus oxychloride (POCl3, 5.2 mL, 56.8 mmol) at 25 °C. Subsequently, the reaction mixture was heated to 80 °C and stirred at this temperature for 3.0 hours. Upon completion of the reaction, the mixture was cooled to 25 °C and diluted with the addition of toluene (100 mL). The organic phase was separated, washed with ice water (50 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated by decompression to afford the title compound 4-chloro-6-nitroquinazoline as a yellow solid (7.00 g, 64.2% yield).
The structure of the compound was confirmed by the following spectral data: 1H NMR (400 MHz, DMSO-d6) δ: 8.78 (s, 1H), 8.54 (d, J = 6.8 Hz, 1H), 8.39 (s, 1H), 7.87 (d, J = 12.4 Hz, 1H). | [References]
[1] Patent: CN108373452, 2018, A. Location in patent: Paragraph 0010; 0024; 0036-0041; 0050-0053
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 3974 - 3980
[3] Chinese Journal of Chemistry, 2014, vol. 32, # 6, p. 538 - 544
[4] Patent: WO2014/177038, 2014, A1. Location in patent: Paragraph 00255-00256
[5] Tetrahedron Letters, 2012, vol. 53, # 6, p. 674 - 677 |
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