| Identification | More | [Name]
2-Fluoro-4-hydroxybenzaldehyde | [CAS]
348-27-6 | [Synonyms]
2-FLUORO-4-HYDROXYBENZALDEHYDE
2-FLURO-4-HYDROXYBENZALDEHYDE | [Molecular Formula]
C7H5FO2 | [MDL Number]
MFCD06797918 | [Molecular Weight]
140.11 | [MOL File]
348-27-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
168-170°C | [Boiling point ]
254.2±20.0 °C(Predicted) | [density ]
1.350±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
crystalline powder | [pka]
6.78±0.18(Predicted) | [color ]
Light tan | [InChI]
InChI=1S/C7H5FO2/c8-7-3-6(10)2-1-5(7)4-9/h1-4,10H | [InChIKey]
ONRPXRPUBXXCCM-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=C(O)C=C1F | [CAS DataBase Reference]
348-27-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
2-Fluoro-4-hydroxybenzaldehyde is a useful reagent for preparation of 3,4-ring fused 7-azaindoles and deazapurines as potent JAK2 inhibitors. | [Synthesis]
Preparation of 2-fluoro-4-hydroxybenzaldehyde involves: (1) mixing 3-fluorophenol (I), potassium carbonate, and 2-bromopropane in an organic solvent, and heating to react to obtain 1-fluoro-3-isopropoxybenzene (II); (2) dissolving compound (II) in an organic solvent and reacting with a brominating reagent to obtain 1-bromo-2-fluoro-4-isopropoxybenzene (III); (3) dissolving compound (III) in tetrahydrofuran, dripping isopropylmagnesium chloride/tetrahydrofuran solution at -10°C to 0°C, adding dimethylformamide to react after Grignard exchange to obtain 2-fluoro-4-isopropoxybenzaldehyde (IV); and (4) reacting compound (IV) with boron trichloride and deprotecting.
| [References]
[1] Patent: US2011/98251, 2011, A1. Location in patent: Page/Page column 67-68
[2] Chemistry Letters, 2008, vol. 37, # 4, p. 436 - 437
[3] Patent: WO2007/14895, 2007, A2. Location in patent: Page/Page column 30; 31
[4] Patent: WO2008/87198, 2008, A1. Location in patent: Page/Page column 44-45
[5] Patent: WO2010/102154, 2010, A2. Location in patent: Page/Page column 55 |
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