2-FLUORO-3-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

47-51 °C (lit.)

Boiling point:

239.9±20.0 °C(Predicted)

Density 

1.192±0.06 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

Inert atmosphere,2-8°C

form 

claggy powder

color 

Sandy beige

Sensitive 

Air Sensitive

CAS DataBase Reference

103438-88-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-43

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich

2-FLUORO-3-METHOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

White to yellow crystalline solid

Uses

2-Fluoro-3-methoxybenzaldehyde is an intermediate in the synthesis of benzylidene-1,3-thiazolidine-2,4-diones as potent and selective inhibitors of the PIM-1, PIM-2, and PIM-3 protein kinases.

Synthesis

GENERAL STEPS: To a solution of 2-fluoro-3,N-dimethoxy-N-methylbenzamide (2.30 g, 10.8 mmol) in tetrahydrofuran (THF, 20 mL) was slowly added a toluene solution of 1 M diisobutylaluminum hydride (DIBAL-H) (12 mL, 12 mmol) at -78°C. The reaction mixture was stirred at -78 °C for 3 h before an additional toluene solution of 1 M DIBAL-H (4.2 mL, 4.2 mmol) was added. Stirring was continued at -78 °C for 30 min, followed by slow warming of the reaction mixture to room temperature. Upon completion of the reaction, the reaction was carefully quenched with saturated aqueous ammonium chloride (NH4Cl) solution. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were washed sequentially with 1 N hydrochloric acid (HCl) and saturated brine. The organic phase was dried with anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a gradient of mixed solvents of ethyl acetate (EtOAc) and hexane (0:100 to 1:1) to afford the target compound 2-fluoro-3-methoxybenzaldehyde (1.41 g, 85% yield).1H NMR (300 MHz, CDCl3): δ 10.38 (1H, s), 7.43-7.40 (1H, m) , 7.24-7.15 (2H, m), 3.95 (3H, s).

References

[1] Patent: WO2004/43903, 2004, A1. Location in patent: Page 66 - 67
[2] Patent: WO2004/43904, 2004, A1. Location in patent: Page 62 - 63
[3] Patent: WO2004/43931, 2004, A1. Location in patent: Page 40-41

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