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

form 

solid

pka

13.75±0.30(Predicted)

color 

Brown

CAS DataBase Reference

6625-96-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

Hazard Note 

Irritant

HS Code 

2933998090

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(6625-96-3)Related Product Information

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• 2-Nitrobenzaldehyde
• 3-Nitrobenzaldehyde
• Indometacin
• 3-Nitrotoluene
• 5-Nitroindole
• Indole-3-acetic acid
• 5-NITROINDOLE-3-CARBOXYLIC ACID
• 3-CYANO-5-NITROINDOLE
• NITROGEN DIOXIDE
• 2-METHYL-5-NITRO-1H-INDOLE-3-CARBALDEHYDE
• 5-METHOXY-1-METHYL-4-NITROINDOLE-3-CARBOXALDEHYDE
• 7-NITRO-1H-INDOLE-3-CARBALDEHYDE
• 2-[(4-BROMOPHENYL)SULFANYL]-1-METHYL-5-NITRO-1H-INDOLE-3-CARBALDEHYDE
• 3-FORMYL-5-NITROINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-FORMYL-5-NITRO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 1-(5-nitro-1H-indol-3-yl)propan-1-one
• 4-NITRO-1H-INDOLE-3-CARBALDEHYDE