2-Fluoro-4-methoxybenzaldehyde Chemical Properties

Melting point:

43-48 °C (lit.)

Boiling point:

226.5±20.0 °C(Predicted)

Density 

1.192±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

powder to crystal

color 

White to Brown

Sensitive 

Air Sensitive

BRN 

3237954

InChI

InChI=1S/C8H7FO2/c1-11-7-3-2-6(5-10)8(9)4-7/h2-5H,1H3

InChIKey

UNWQNFJBBWXFBG-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

331-64-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Fluoro-4-methoxybenzaldehyde Usage And Synthesis

Chemical Properties

white to off-white crystalline solid

Uses

2-Fluoro-4-methoxybenzaldehyde may be used in the preparation of:

• fluorine containing 2,4,5-trisubstituted imidazole
• 1-(2-fluoro-4-methoxyphenyl)-2-propanone
• 6-(2-fluoro-4-methoxyphenyl)fulvene
• 10-(2-fluoro-4-methoxyphenyl)-6,7,9,10-tetrahydro-1Hfuro[3,4-b]pyrazolo[3,4-f]quinolin-9-one
• polyhydroquinoline (PHQ)
• 3-(2-fluoro-4-methoxyphenyl) acrylic acid methyl ester

Uses

2-Fluoro-4-methoxybenzaldehyde was used in the synthesis of new analogues as inhibitors for phosphodiesterase 10A.

General Description

2-Fluoro-4-methoxybenzaldehyde is a fluorinated aromatic aldehyde. It can be prepared from 4-bromo-3-fluoroanisole.

Synthesis

The general procedure for the synthesis of 2-fluoro-4-methoxybenzaldehyde from pyridine trioxide and 2-fluoro-4-methoxybenzyl alcohol was as follows: triethylamine (0.92 mL, 6.60 mmol) was added to a solution of 2-fluoro-4-methoxybenzyl alcohol (346.9 mg, 2.22 mmol) in DMSO (8 mL). Subsequently, pyridine sulfur trioxide (1.0501 g, 6.60 mmol) was added to the mixture in batches and the change in reaction temperature was monitored. The reaction mixture was stirred for 0.5 hours. After completion of the reaction, the mixture was poured into 5% aqueous KHSO4 solution and extracted three times with ethyl acetate, the organic layers were combined and dried over anhydrous MgSO4. The organic layer was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: hexane/ether=5/1) to afford the target compound 2-fluoro-4-methoxybenzaldehyde (301 mg, 88% yield). The product was characterized by 1H-NMR (CDCl3): δ 10.21 (s, 1H), 7.83 (t, 1H, J=8.3 Hz), 6.79 (ddd, 1H, J=8.3, 2.3, 0.7 Hz), 6.65 (dd, 1H, J=12.2, 2.3 Hz), 3.88 (s, 3H).

References

[1] Patent: US6194461, 2001, B1

2-Fluoro-4-methoxybenzaldehyde(331-64-6)Related Product Information

• o-Anisaldehyde
• (Trifluoromethoxy)benzene
• 2,4-Dimethoxybenzaldehyde
• Veratraldehyde
• 2-(Trifluoromethyl)benzaldehyde
• 3-Methoxybenzaldehyde
• 3-(Trifluoromethyl)benzaldehyde
• 2,5-Dimethoxybenzaldehyde
• 2,3-Dimethoxybenzaldehyde
• 2,6-Dimethoxybenzaldehyde
• 4-Hydroxybenzaldehyde
• 4-(Trifluoromethoxy)aniline
• 3,5-Dimethoxybenzaldehyde
• Benzaldehyde
• p-Anisaldehyde
• Fluorine
• 2-Fluoro-4-methoxyacetophenone
• 6-FLUOROVERATRALDEHYDE