Identification | Back Directory | [Name]
5-BROMO-6-FLUORO-1H-INDAZOLE | [CAS]
105391-70-6 | [Synonyms]
5-BroMo-6-fluoro-1H- 5-BROMO-6-FLUOROINDAZOLE 5-BROMO-6-FLUORO-1H-INDAZOLE 1H-Indazole, 5-bromo-6-fluoro- | [Molecular Formula]
C7H4BrFN2 | [MDL Number]
MFCD11044589. | [MOL File]
105391-70-6.mol | [Molecular Weight]
215.02 |
Chemical Properties | Back Directory | [Boiling point ]
332.2±22.0 °C(Predicted) | [density ]
1.861 | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
11.95±0.40(Predicted) | [Appearance]
Off-white to light brown Solid | [InChI]
InChI=1S/C7H4BrFN2/c8-5-1-4-3-10-11-7(4)2-6(5)9/h1-3H,(H,10,11) | [InChIKey]
ZNNFNEIFQIAWNY-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(Br)C(F)=C2)C=N1 |
Hazard Information | Back Directory | [Uses]
5-Bromo-6-fluoro-1H-indazole is used for optimization and biological evaluation of [(trifluoromethyl)phenyl]indazoles as TRPA1 antagonists. | [Synthesis]
General procedure for the synthesis of 5-bromo-6-fluoro-1H-indazole from 1-(5-bromo-6-fluoro-1H-indazol-1-yl)ethanone: 1-(5-bromo-6-fluoro-1H-indazol-1-yl)ethanone (1.58 g, 6.15 mmol) was dissolved in a solvent mixture of a 3M HCl aqueous solution (20 mL) and methanol (4 mL). The reaction mixture was heated to reflux at 90 °C for 3 hours. Upon completion of the reaction, it was cooled to room temperature and the pH was adjusted to 10 with 1 M NaOH aqueous solution. at this point, a colorless solid precipitated from the solution, which was collected by filtration and dried under vacuum to afford the target product 5-bromo-6-fluoro-1H-indazole (1.22 g, 93% yield). The 1H NMR (CDCl3) data of the product were as follows: δ 9.0-10.20 (1H, br), 8.02 (1H, s), 7.97 (1H, d, J = 6.4 Hz), 7.28 (1H, s). | [References]
[1] Patent: WO2012/103806, 2012, A1. Location in patent: Page/Page column 55 [2] Patent: WO2006/44860, 2006, A2. Location in patent: Page/Page column 37-38 [3] Patent: US2016/347717, 2016, A1. Location in patent: Paragraph 0619; 0620 [4] Patent: WO2009/32123, 2009, A2. Location in patent: Page/Page column 179-180 [5] Patent: WO2009/32125, 2009, A1. Location in patent: Page/Page column 119 |
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