| Identification | Back Directory | [Name]
4-fluoro-2-hydroxybenzonitrile | [CAS]
186590-01-2 | [Synonyms]
4-fluoro-2-hydroxybenzonitrile
4-Fluoro-2-hydroxybenzonitrile 98%
4-Fluorosalicylonitrile, 2-Cyano-5-fluorophenol | [Molecular Formula]
C7H4FNO | [MDL Number]
MFCD13185487 | [MOL File]
186590-01-2.mol | [Molecular Weight]
137.11 |
| Chemical Properties | Back Directory | [Boiling point ]
266.5±25.0 °C(Predicted) | [density ]
1.34±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [pka]
6.17±0.10(Predicted) | [Appearance]
Off-white to light brown Solid | [InChI]
InChI=1S/C7H4FNO/c8-6-2-1-5(4-9)7(10)3-6/h1-3,10H | [InChIKey]
ZAYFMRICIYQIAP-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=C(F)C=C1O |
| Hazard Information | Back Directory | [Uses]
2-Cyano-5-fluorophenol is used in the study of substituent effect on fluorobenzene derivatives on cytochrome P 450-catalyzed hydroxylation at adjacent ortho aromatic carbon center. | [Synthesis]
General procedure for the synthesis of 4-fluoro-2-hydroxybenzonitrile from 2-methoxy-4-fluorobenzonitrile: A mixture of 4-fluoro-2-methoxybenzonitrile (4.53 g, 30 mmol) and aluminum trichloride (5.0 g, 37.6 mmol; purchased from Aldrich) in anhydrous toluene (30 mL) was stirred and reacted for 18 hours at 130 °C. After completion of the reaction, the mixture was cooled to room temperature, ice water (~50 mL) was added, and extracted with ether (20 mL × 2). The organic phases were combined, washed sequentially with water and saturated brine, and then dried with anhydrous magnesium sulfate. After concentration under reduced pressure, 4-fluoro-2-hydroxybenzonitrile (3.90 g, 28.5 mmol, 95% yield) was obtained as a white solid. Its structure was confirmed by the following characterization: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-H), 7.71 (1H, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 MHz) δ ppm: 95.13, 102.45, 102.78, 106.53, 106.83, 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35. The calculated value of the high-resolution mass spectrometry (ESI-) for C7H3NOF (M-H) was 136.0199 and the measured value was 136.0199. | [References]
[1] Patent: US2005/267105, 2005, A1. Location in patent: Page/Page column 67
[2] Patent: US2007/111984, 2007, A1. Location in patent: Page/Page column 33
[3] Patent: WO2007/64316, 2007, A1. Location in patent: Page/Page column 153
[4] Patent: WO2007/39172, 2007, A1. Location in patent: Page/Page column 157-158
[5] Patent: US2008/261979, 2008, A1. Location in patent: Page/Page column 74 |
|
|