4-FLUORO-2-HYDROXYBENZALDEHYDE Chemical Properties

Melting point:

70-72°C

Boiling point:

208.2±20.0 °C(Predicted)

Density 

1.350±0.06 g/cm3(Predicted)

Flash point:

110°

storage temp. 

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

form 

crystalline solid

pka

7.18±0.10(Predicted)

color 

Pale yellow

Sensitive 

Air Sensitive

CAS DataBase Reference

348-28-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

Hazard Note 

Irritant

HS Code 

29122990

4-FLUORO-2-HYDROXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

Solid

Uses

4-Fluorosalicylaldehyde is used as a reagent to synthesize quinoline derivatives that have potential antibacterial and antituberculosis effects. 4-Fluorosalicylaldehyde is also used as a reagent to prepare chromones (e.g. 4-Oxo-4H-1-benzopyran-2-carboxylic acid [B205670]).

Synthesis

The general procedure for the synthesis of 4-fluoro-2-hydroxybenzaldehyde from formaldehyde and 3-fluorophenol was as follows: to a mixture containing 3-fluorophenol (5 mL, 55.3 mmol) and anhydrous acetonitrile (250 mL) were added MgCl2 (14.2 g, 149 mmol), anhydrous trimethylamine (27 mL) and paraformaldehyde (11 g). The reaction mixture was stirred under reflux conditions for 5 h and subsequently cooled to room temperature. The reaction was quenched by addition of 5% hydrochloric acid (250 mL) and extracted with ethyl acetate (100 mL × 3). The combined organic layers were washed sequentially with 5% hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 50:1 to 20:1) to afford 4-fluoro-2-hydroxybenzaldehyde (5 g, 65% yield) as a light yellow solid.1H NMR (400 MHz, CDCl3) data were as follows: δ 11.37 (d, J = 1.6 Hz, 1H), 9.83 (s, 1H), 7.55- 7.59 (m, 1H), 6.65-6.75 (m, 2H).

References

[1] Patent: WO2004/87686, 2004, A2. Location in patent: Page 504
[2] Patent: WO2004/87687, 2004, A1. Location in patent: Page 504
[3] Patent: WO2017/55860, 2017, A1. Location in patent: Page/Page column 138-139
[4] Patent: US2017/37038, 2017, A1. Location in patent: Paragraph 0375; 0376; 0377
[5] Patent: KR101679262, 2016, B1. Location in patent: Paragraph 0156-0158

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