Ethyl 5-nitroindole-2-carboxylate Chemical Properties

Melting point:

220-225 °C

Boiling point:

376.52°C (rough estimate)

Density 

1.3240 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Powder

pka

13.26±0.30(Predicted)

color 

Yellow to brown

Water Solubility 

negligible

CAS DataBase Reference

16732-57-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-36

Safety Statements 

24/25-39-26

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:ACROS

Ethyl 5-nitroindole-2-carboxylate Usage And Synthesis

Uses

Ethyl 5-Nitroindole-2-carboxylate is used as a reagent in the synthesis of indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors. Ethyl 5-Nitroindole-2-carboxylate is also a useful synthetic intermediate in the synthesis of Delavirdine which is a bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.

Chemical Properties

yellow to brown powder

Uses

Ethyl 5-Nitroindole-2-carboxylate is used as a reagent in the synthesis of indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors. Ethyl 5-Nitroindole-2-carboxylate is also a useful synthetic intermediate in the synthesis of Delavirdine (D230625) which is a bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.

Synthesis

To a dry 500 mL three-necked flask, ethyl 2-[2-(4-nitrophenyl)hydrazinylidene]propionate (10 g, 0.042 mol) was added sequentially. Polyphosphoric acid (110 g) was slowly heated to 100 °C under mechanical stirring. The reaction was maintained at this temperature for 2 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After confirming the completion of the reaction, the heating was stopped. The reaction mixture was cooled to room temperature and the reaction was quenched by slowly pouring it into a large amount of ice water. The precipitate was collected by filtration and the filter cake was washed with cold water. The resulting green solid product, ethyl 5-nitroindole-2-carboxylate, was dried in a vacuum drying oven to give 8.9 g in 90.2% yield.

References

[1] Patent: CN107739368, 2018, A. Location in patent: Paragraph 0036; 0038; 0040
[2] Synthesis, 1980, # 3, p. 222 - 223
[3] Patent: US9226970, 2016, B2. Location in patent: Page/Page column 39
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[5] Farmaco, Edizione Scientifica, 1958, vol. 13, p. 105,109

Ethyl 5-nitroindole-2-carboxylate(16732-57-3)Related Product Information

• Diethyl nitromalonate
• 5-Nitroindole
• Indole-3-butyric acid
• Indole-3-acetic acid
• Indole-2-carboxylic acid
• Diethyl 1,3-acetonedicarboxylate
• ISOXADIFEN-ETHYL
• Indometacin
• Ethyl cyanoacetate
• Ethylparaben
• RESMETHRIN
• Ethyl acrylate
• Ethyl formate
• Ethyl pyruvate
• Ethanol
• Ethyl acetate
• 5-Nitroindole-2-carboxylic acid
• ETHYL 7-NITROINDOLE-2-CARBOXYLATE