7-NITROINDOLE-3-CARBOXALDEHYDE Chemical Properties

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

12.47±0.30(Predicted)

form 

Solid

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C9H6N2O3/c12-5-6-4-10-9-7(6)2-1-3-8(9)11(13)14/h1-5,10H

InChIKey

ADGKBVRTGVODMM-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2[N+]([O-])=O)C(C=O)=C1

CAS DataBase Reference

10553-14-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933998090

7-NITROINDOLE-3-CARBOXALDEHYDE Usage And Synthesis

Synthesis

Phosphorus oxychloride (POCl3, 0.418 mL, 3.13 mmol) was slowly added dropwise to N,N-dimethylformamide (DMF, 2.08 mL) at 0°C and under argon protection. After stirring the reaction mixture for 5 min, a DMF solution of 7-nitroindole (200 mg, 1.25 mmol) was added (at a concentration of 10 mL of DMF per 1 g of indole). Subsequently, the reaction mixture was gradually warmed to room temperature and stirring was continued for 3 hours. After completion of the reaction, 3.8 M aqueous potassium hydroxide solution (3.29 mL, 12.5 mmol) was added to the mixture and stirring was continued for 15 hours. Next, saturated aqueous sodium bicarbonate and ethyl acetate (EtOAc) were added to the reaction system until the mixture became clarified, followed by separation of the organic layer. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. Finally, the residue was purified by silica gel column chromatography (eluent ratio hexane/ethyl acetate = 1/5) to afford the target product 7-nitroindole-3-carbaldehyde (228 mg, 1.20 mmol, 96% yield) as a yellow amorphous solid.

References

[1] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 8, p. 810 - 817
[2] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[3] Tetrahedron Letters, 2009, vol. 50, # 1, p. 75 - 76
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 23, p. 7541 - 7551
[5] Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2362 - 2372

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