| Identification | More | [Name]
Ethyl 5-nitroindole-2-carboxylate | [CAS]
16732-57-3 | [Synonyms]
5-NITROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
ETHYL 5-NITRO-1H-INDOLE-2-CARBOXYLATE
ETHYL 5-NITRO-2-CARBOXYLATE
ETHYL 5-NITROINDOLE-2-CARBOXYLATE
LABOTEST-BB LT00441291
OXALIC ACID MONO-(N-METHYL)-AMIDE
Ethyl 5-Nitro Indole-2-Carbonate
5-Nitroindole-2-Carboxylic
5-Nitroindole-2-carboxylate
Ethyl 5-nitro-1H-indole-2-carboxylate ,98% | [Molecular Formula]
C11H10N2O4 | [MDL Number]
MFCD06245498 | [Molecular Weight]
234.21 | [MOL File]
16732-57-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to brown powder | [Melting point ]
220-225 °C
| [Boiling point ]
376.52°C (rough estimate) | [density ]
1.3240 (rough estimate) | [refractive index ]
1.5300 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Powder | [pka]
13.26±0.30(Predicted) | [color ]
Yellow to brown | [Water Solubility ]
negligible | [Detection Methods]
HPLC,NMR,MS | [CAS DataBase Reference]
16732-57-3(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow to brown powder | [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 |
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