4-FLUOROCINNAMALDEHYDE

4-FLUOROCINNAMALDEHYDE Property

Boiling point:

245.6±15.0 °C(Predicted)

Density 

1.146 g/mL at 25 °C

refractive index 

n20/D 1.599

Flash point:

>110°C

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

liquid

Safety

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

4-FLUOROCINNAMALDEHYDE Chemical Properties,Usage,Production

Uses

trans-4-Fluorocinnamaldehyde is a reagent used in the preparation of novel terminal bipheny-based diapophytoene desaturases which are used in the treatment of Staphylococcus aureus infections.

Synthesis

GENERAL STEPS: 4-Fluorobenzaldehyde (9.40 g, 75.8 mmol) and formylmethylenetriphenylphosphorane (30.0 g, 98.6 mmol) were suspended in toluene (150 mL), and the reaction was stirred for 12 hours at 70 °C. After completion of the reaction, the reaction mixture was treated with ethyl acetate (EtOAc) and water (H2O). The organic layer was separated, washed with saturated saline (brine), dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure. The residue was purified by column chromatography to afford unsaturated aldehyde (8.04 g, 71% yield). The resulting aldehyde (8.04 g, 53.5 mmol) was dissolved in a solvent mixture of pyridine (100 mL) and dichloromethane (50 mL) at 0 °C and iodine monochloride (17.4 g, 107 mmol) was added. After stirring at 0 °C for 5 h, the reaction was quenched with aqueous sodium thiosulfate (Na2S2O3) and treated with ethyl acetate (EtOAc). The organic layer was separated, washed with saturated saline (brine), dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure. The residue was purified by column chromatography to afford p-fluorocinnamaldehyde (10.01 g, 68% yield).1H-NMR (300 MHz, DMSO-d6) δ: 7.43 (2H, t, J = 8.5 Hz), 8.13 (2H, dd, J = 8.5, 5.5 Hz), 8.54 (1H, s), 8.84 (1H, s).

References

[1] Patent: WO2007/77961, 2007, A2. Location in patent: Page/Page column 302-303
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 8, p. 1910 - 1913
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 3, p. 719 - 725