| Identification | Back Directory | [Name]
4,6-DIFLUOROINDOLINE-2,3-DIONE | [CAS]
126674-93-9 | [Synonyms]
BUTTPARK 50\07-84
4,6-DIFLUOROISATIN
6-DIFLUOROINDOLINE-2
4,6-DIFLUOROINDOLINE-2,3-DIONE
4,6-Difluoro-2,3-dioxoindoline
1H-Indole-2,3-dione, 4,6-difluoro-
4,6-difluoro-2,3-dihydro-1H-indole-2,3-dione
4,6-Difluoro isatin 4,6-Difluoro indole-2,3-dione
4,6-DIFLUOROINDOLINE-2,3-DIONE ISO 9001：2015 REACH | [Molecular Formula]
C8H3F2NO2 | [MDL Number]
MFCD03618552 | [MOL File]
126674-93-9.mol | [Molecular Weight]
183.11 |
| Chemical Properties | Back Directory | [Melting point ]
218-220 °C | [density ]
1.578 | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
7.65±0.20(Predicted) | [Appearance]
Light yellow to green yellow Solid | [InChI]
InChI=1S/C8H3F2NO2/c9-3-1-4(10)6-5(2-3)11-8(13)7(6)12/h1-2H,(H,11,12,13) | [InChIKey]
YIVXDNUTNIKQMY-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(F)=CC(F)=C2)C(=O)C1=O | [LogP]
1.13 |
| Hazard Information | Back Directory | [Uses]
4,6-DIFLUOROINDOLINE-2, 3-dione (126674-93-9), also known as 4,6-difluoroisatin, is a fluorinated derivative of indole. It is primarily used as a synthetic intermediate in the production of specialised pharmaceuticals and agrochemicals, such as anti-cancer Kras G12C inhibitors and CRHR2 antagonists for the treatment of chronic heart failure. | [Synthesis]
Stage 2: Synthesis of 4,6-difluoro-1H-indole-2,3-dione
The product of stage 1, 2-hydroxyimino-N-(3,5-difluorophenyl)-acetamide (21.1 g, 105 mmol) was slowly added to concentrated sulfuric acid (115 ml) preheated to 50-60°C. After maintaining this temperature and stirring for 15 minutes, the reaction mixture was warmed up to 100°C and stirring was continued for 30 minutes. After completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice (1.2 kg). The precipitated solid was collected by filtration, washed to neutrality with plenty of water and finally dried in a desiccator using phosphorus pentoxide as desiccant. The yellow solid product 4,6-difluoro-1H-indole-2,3-dione was obtained 18.4 g in 95% yield.
1H-NMR (DMSO-d6) data: δ 6.60 (1H, dd, J = 8.8 and 2.0 Hz); 6.84 (1H, dt, J = 9.8 and 2.0 Hz); 11.20 (1H, br s). | [References]
[1] Patent: US2008/293749, 2008, A1. Location in patent: Page/Page column 14 |
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