| Identification | Back Directory | [Name]
Benzaldehyde, 2,4-difluoro-6-hydroxy- (9CI) | [CAS]
136516-64-8 | [Synonyms]
4,6-Difluoro-2-hydroxybenzaldehyde
Benzaldehyde, 2,4-difluoro-6-hydroxy-
Benzaldehyde, 2,4-difluoro-6-hydroxy- (9CI) | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C7H4F2O2 | [MDL Number]
MFCD03701048 | [MOL File]
136516-64-8.mol | [Molecular Weight]
158.1 |
| Chemical Properties | Back Directory | [Melting point ]
32℃ | [Boiling point ]
207.6±35.0 °C(Predicted) | [density ]
1.464±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
6.18±0.15(Predicted) | [InChI]
InChI=1S/C7H4F2O2/c8-4-1-6(9)5(3-10)7(11)2-4/h1-3,11H | [InChIKey]
MIHBQNSVCKHGOA-UHFFFAOYSA-N | [SMILES]
C(=O)C1=C(O)C=C(F)C=C1F |
| Hazard Information | Back Directory | [Synthesis]
Step A: 3,5-difluorophenol (2.6 g, 20 mmol) was dissolved in acetonitrile (50 mL) and triethylamine (14 mL, 100 mmol) was added. Magnesium chloride (3.8 g, 40 mmol) and paraformaldehyde (6.4 g, 200 mmol) were then added sequentially. The resulting inhomogeneous mixture was reacted at 60 °C with vigorous stirring for 16 hours. Upon completion of the reaction, the mixture was diluted with deionized water (200 mL) and the pH was adjusted to <2 with 1 M aqueous hydrochloric acid. the reaction mixture was extracted with ethyl acetate (200 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2,4-difluoro-6-hydroxybenzaldehyde (2.6 g, 82% yield) as a red oily product. Mass spectrometry analysis showed m/z 157.1 [M-H]-. | [References]
[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 4, p. 1473 - 1482
[2] Patent: WO2013/101974, 2013, A1. Location in patent: Paragraph 00614; 00615
[3] Patent: US9617268, 2017, B2. Location in patent: Page/Page column 327; 328 |
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