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| | 5-Nitro-1H-indole-3-carbaldehyde Basic information | | Application |
| Product Name: | 5-Nitro-1H-indole-3-carbaldehyde | | Synonyms: | 5-NITROINDOLE-3-ALDEHYDE;5-NITROINDOLE-3-CARBOXALDEHYDE;5-NITRO-1H-INDOLE-3-CARBALDEHYDE;RARECHEM AH BS 0125;5-Nitroindole-3-carbaldehyde;3-Formyl-5-nitro-1H-indole;5-Nitro-1H-indole-3-carboxaldehyde;5-nitro-2H-indazole-3-carboxaldehyde | | CAS: | 6625-96-3 | | MF: | C9H6N2O3 | | MW: | 190.16 | | EINECS: | | | Product Categories: | Indole | | Mol File: | 6625-96-3.mol |  |
| | 5-Nitro-1H-indole-3-carbaldehyde Chemical Properties |
| Melting point | 300 °C | | Boiling point | 441.5±25.0 °C(Predicted) | | density | 1.516±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 13.75±0.30(Predicted) | | form | solid | | color | Brown | | CAS DataBase Reference | 6625-96-3(CAS DataBase Reference) |
| | 5-Nitro-1H-indole-3-carbaldehyde Usage And Synthesis |
| Application | 5-Nitroindole-3-carboxaldehyde can be used as a pharmaceutical synthesis intermediate. It can be prepared from 5-nitro-1H-indole as a reactant and can be used to prepare novel 3,5-disubstituted 1H-indole derivatives. It has good inhibitory activity against the pancreatic cancer cell line BxPC-3. | | Synthesis | Phosphorus oxychloride (POCl3, 0.31 mL, 3.39 mmol, 1.1 eq.) was slowly added dropwise to dry N,N-dimethylformamide (DMF, 2 mL) under argon protection, and the reaction system was cooled to -20 °C with vigorous stirring.After 30 min, 5-nitroindole (500 mg, 3.08 mmol, 1 eq.) dissolved in 0.5 mL of anhydrous DMF was slowly added to the above solution cooled to -20 °C. The reaction was carried out in the same manner as that for the reaction. mmol, 1 equiv) was slowly added to the above solution cooled to -20 °C. Subsequently, the resulting yellow solution was stirred at room temperature for 1 h. The light yellow compound was observed to precipitate. The reaction mixture was diluted with DMF and an equal volume of ice water was added. Next, the pH was adjusted to 9 by dropwise addition of 50% (v/v) aqueous sodium hydroxide solution, and the resulting red solution was refluxed and subsequently allowed to stand at 4 °C overnight. The precipitated crystals were collected by filtration, washed with cold water and dried. Recrystallization by ethanol-water (EtOH-H2O) system afforded 574 mg of 5-nitroindole-3-carbaldehyde (compound XV) in 98% yield.1H-NMR (400 MHz, DMSO-d6) δ ppm: 7.69 (d, J = 9.0 Hz, 1H), 8.12 (dd, J = 2.3 Hz, 1H), 8.54 (s, 1H ), 8.91 (d, 1H), 9.99 (s, 1H). | | References | [1] Patent: EP2003129, 2008, A1. Location in patent: Page/Page column 16
[2] Patent: CN107915726, 2018, A. Location in patent: Paragraph 0047-0050
[3] Organic Letters, 2008, vol. 10, # 12, p. 2601 - 2604
[4] Organic Letters, 2014, vol. 16, # 4, p. 1268 - 1268
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 33, p. 5721 - 5725 |
| | 5-Nitro-1H-indole-3-carbaldehyde Preparation Products And Raw materials |
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