5-NITROINDOLE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

276-278 °C (decomp)

Boiling point:

520.8±30.0 °C(Predicted)

Density 

1.632±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.38±0.30(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C9H6N2O4/c12-9(13)7-4-10-8-2-1-5(11(14)15)3-6(7)8/h1-4,10H,(H,12,13)

InChIKey

OOOJXNVTVWRZMA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6958-37-8(CAS DataBase Reference)

5-NITROINDOLE-3-CARBOXYLIC ACID Usage And Synthesis

Synthesis Reference(s)

Journal of Medicinal Chemistry, 35, p. 1019, 1992 DOI: 10.1021/jm00084a007

Synthesis

1-(5-nitro-3-indolyl)-2,2,2-trifluoroethanone (7 g, 24.7 mmol) was used as the raw material, which was dissolved in 40% aqueous NaOH solution (40 mL), and the reaction was stirred for 3 hours at 60 °C. After completion of the reaction, the reaction mixture was cooled to 0 °C and acidified by slowly adding 1N HCl aqueous solution to adjust the pH to ~3. Subsequently, the precipitate was collected by filtration, the filter cake was washed with water, and finally the target product 5-nitroindole-3-carboxylic acid (5.9 g, 100% yield) was obtained by concentration as a brown solid. The product was detected by LC/MS (ESI), m/z: 207 [M + 1]+.

References

[1] Patent: WO2017/35351, 2017, A1. Location in patent: Paragraph 0584; 0585; 0586
[2] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 3006 - 3016

5-NITROINDOLE-3-CARBOXYLIC ACID(6958-37-8)Related Product Information

• 3-CYANO-5-NITROINDOLE
• 5-Nitro-1H-indole-3-carbaldehyde
• 4-NITROINDOLE-3-CARBOXYLIC ACID
• 5-NITROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 5-NITROINDOLE-3-CARBOXYLIC ACID
• 7-NITROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 5-NITROINDOLE-2-CARBOXYLIC ACID
• 7-NITROINDOLE-2-CARBOXYLIC ACID,7-Nitroindole-2-carboxylic acid, 90-95%
• 5-Nitroindole
• 4-NITROINDOLE-2-CARBOXYLIC ACID
• 3-HYDROXYMETHYL-5-NITROINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 7-METHOXY-5-NITROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 6-NITROINDOLE-3-CARBOXYLIC ACID
• 3-BROMO-5-NITROINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-FORMYL-5-NITROINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-IODO-5-NITROINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 6-NITROINDOLE-2-CARBOXYLIC ACID
• 3-BROMO-7-NITROINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER