| Identification | More | [Name]
5-NITROINDOLE-3-CARBOXYLIC ACID | [CAS]
6958-37-8 | [Synonyms]
5-NITROINDOLE-3-CARBOXYLIC ACID
RARECHEM AL BE 1168 | [Molecular Formula]
C9H6N2O4 | [MDL Number]
MFCD06203492 | [Molecular Weight]
206.15 | [MOL File]
6958-37-8.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
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