2-FLUORO-5-HYDROXYBENZALDEHYDE Chemical Properties

Melting point:

74-75 °C

Boiling point:

257.6±20.0 °C(Predicted)

Density 

1.350±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

9.25±0.18(Predicted)

Appearance

White to light brown Solid

InChI

InChI=1S/C7H5FO2/c8-7-2-1-6(10)3-5(7)4-9/h1-4,10H

InChIKey

SNILBNSNKISKLU-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(O)=CC=C1F

Safety Information

HS Code 

2912490090

2-FLUORO-5-HYDROXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

2-Fluoro-5-hydroxybenzaldehyde is solid at room temperature and pressure, with weak acidity and good chemical reaction activity, it is difficult to dissolve in water but can be dissolved in common organic solvents, including ethyl acetate, dichloromethane and so on.

Uses

2-Fluoro-5-hydroxybenzaldehyde is used in the enantioselective synthesis of 1,?1''-?spirobiindane-?7,?7''-?diol (SPINOL) derivatives.

Synthesis

General procedure for the synthesis of 2-fluoro-5-hydroxybenzaldehyde from 2-fluoro-5-methoxybenzaldehyde: Step 1: BBr3 (4 mL, 4 mmol, 1.0 M solution in heptane) was slowly added dropwise to a dichloromethane solution of 2-fluoro-5-methoxybenzaldehyde at -78 °C. The reaction mixture was stirred continuously at -78 °C for 1 hour, followed by slow warming to 0 °C and continued stirring for 2 hours. Upon completion of the reaction, the mixture was poured into water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting residue was purified by silica gel column chromatography with 0-20% ethyl acetate-hexane mixed solvent as eluent, resulting in a white solid target product 2-fluoro-5-hydroxybenzaldehyde (142 mg, 25% yield). Mass spectrometry analysis showed m/z 141 [M + H]+.

References

[1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 677 - 694
[2] Patent: WO2005/82890, 2005, A1. Location in patent: Page/Page column 69-70
[3] Patent: US2008/9533, 2008, A1. Location in patent: Page/Page column 17
[4] Patent: WO2005/9940, 2005, A1. Location in patent: Page 183
[5] Patent: WO2013/61052, 2013, A1. Location in patent: Page/Page column 64

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