| Identification | More | [Name]
5-NITROOXINDOLE | [CAS]
20870-79-5 | [Synonyms]
2H-INDOL-2-ONE, 1,3-DIHYDRO-5-NITRO
5-NITRO-1,3-DIHYDROINDOLE-2-ONE
5-NITRO-2-OXINDOLE
5-NITROOXINDOLE
5-Nitrooxindole 96%
5-Nitroindolin-2-one
5-Nitrooxidole | [Molecular Formula]
C8H6N2O3 | [MDL Number]
MFCD00456999 | [Molecular Weight]
178.14 | [MOL File]
20870-79-5.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Keep Cold | [HS Code ]
2933790090 |
| Hazard Information | Back Directory | [Uses]
- Reactant for synthesis of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors
- Reactant for preparation of Aurora kinase inhibitors
- Reactant for synthesis of 3-substituted 2-indolinone RET inhibitors
- Reactant for synthesis of 4-azachromeno[2,3-b]indol-11(6H)-ones and derivatives as analogs of ellipticine
- Reactant for preparation of [18F]fluorobenzylidene-indolinone as possible tyrosine kinase inhibitor for PET tumor imaging
- Reactant for preparation of 3-substituted indolin-2-ones as neuroprotective and toxic agents
| [Synthesis]
General procedure for the synthesis of 5-nitroindol-2-one from 2-indolone: 2-indolone (26 g) was dissolved in 100 mL of concentrated sulfuric acid at -15 °C and fuming nitric acid (8.4 mL) was added slowly and dropwise. The reaction temperature needs to be strictly controlled to ensure that it is maintained at -15 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred for 30 minutes. Subsequently, the reaction solution was carefully poured into ice water and a yellow precipitate was immediately generated. The precipitate was separated by filtration and 34 g of 5-nitroindol-2-one was finally obtained in 98% yield. | [References]
[1] Patent: US2005/256145, 2005, A1. Location in patent: Page/Page column 43
[2] Patent: US2005/256144, 2005, A1. Location in patent: Page/Page column 19
[3] Patent: US2010/75952, 2010, A1. Location in patent: Page/Page column 64
[4] Patent: EP2157093, 2010, A1. Location in patent: Page/Page column 61-62
[5] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 169 |
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