| Identification | Back Directory | [Name]
6-FLUORO-5-NITRO-1H-INDAZOLE | [CAS]
633327-51-2 | [Synonyms]
6-Fluoro-5-nitroindazole
5-nitro-6-fluoro-1H-indazole
6-FLUORO-5-NITRO-1H-INDAZOLE
1H-Indazole, 6-fluoro-5-nitro- | [EINECS(EC#)]
604-604-1 | [Molecular Formula]
C7H4FN3O2 | [MDL Number]
MFCD09261136 | [MOL File]
633327-51-2.mol | [Molecular Weight]
181.12 |
| Chemical Properties | Back Directory | [Boiling point ]
401.2±25.0 °C(Predicted) | [density ]
1.629±0.06 g/cm3(Predicted) | [storage temp. ]
Storage temp. 2-8°C | [pka]
10.92±0.40(Predicted) | [Appearance]
Yellow to orange Solid |
| Hazard Information | Back Directory | [Synthesis]
6-Fluoro-1H-indazole (1 g, 6.74 mmol) was used as a raw material and mixed with concentrated sulfuric acid. Concentrated sulfuric acid (22 mL) and potassium nitrate (0.74 g, 7.34 mmol) were added in batches at 0°C. After addition, stirring was continued for 10 minutes at room temperature. Upon completion of the reaction, the reaction mixture was cooled to 0 °C, alkalized to pH neutral with saturated sodium bicarbonate solution and subsequently extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure to remove the solvent, the crude product was purified by fast column chromatography (eluent: dichloromethane/methanol=9.8:0.2) to afford 6-fluoro-5-nitro-1H-indazole (0.4 g, 30% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ: 13.7 (broad peak, 1H), 8.78 (d, J=7.4 Hz, 1H ), 8.34 (s, 1H), 7.68 (d, J=11.8Hz, 1H). Mass spectrum (ESI) m/z: 180 ([M-H]-). | [References]
[1] Patent: WO2015/104662, 2015, A1. Location in patent: Page/Page column 38
[2] Patent: US2016/326151, 2016, A1. Location in patent: Paragraph 0208
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137 |
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