5-CYANO-2-FLUOROBENZALDEHYDE Chemical Properties

Boiling point:

216.5±20.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

color 

Light yellow to yellow

CAS DataBase Reference

146137-79-3(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2926907090

5-CYANO-2-FLUOROBENZALDEHYDE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-fluoro-3-formylbenzonitrile from p-fluorobenzonitrile is as follows: Example 112 Synthesis of 2-fluoro-5-cyanobenzaldehyde To a stirred solution of cooled diisopropylamine (15.4 mL, 0.11 mol) in anhydrous tetrahydrofuran (200 mL) under argon protection, n-butyllithium (40 mL, 2.5 M hexane solution, 0.11 mol) was slowly added through a dropping funnel over a period of 30 minutes, keeping the reaction temperature at 0°C. The mixture was continued to be stirred at this temperature for 30 minutes. Subsequently, the reaction system was cooled to -78 °C. A solution of anhydrous tetrahydrofuran (50 mL) of 4-fluorobenzonitrile (12.1 g, 0.1 mol) was added dropwise over 15 minutes. The reaction mixture was stirred at -78 °C for 1 h via syringe. Then, dimethylformamide (8 mL) was added dropwise and stirring was continued at -78 °C for 20 min. The reaction was quenched by rapid addition of acetic acid (20 mL) followed by water (500 mL). The product was extracted with ether (2 x 500 mL). The combined organic layers were washed sequentially with 1N HCl, water and saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. After evaporation of the solvent, 2-fluoro-5-cyanobenzaldehyde (11.8 g, 79% yield) was obtained as a light yellow solid. 1H NMR (CDCl3): δ 10.32 (s, 1H), 8.18 (dd, 1H, J = 6.5, 2.5 Hz), 7.88 (m, 1H), 7.33 (t, 1H, J = 9.5 Hz).

References

[1] Patent: US6221914, 2001, B1
[2] Patent: US2002/103229, 2002, A1
[3] Patent: US2004/127536, 2004, A1
[4] Patent: US2005/9876, 2005, A1

5-CYANO-2-FLUOROBENZALDEHYDE(146137-79-3)Related Product Information

• 4-BROMO-3-NITROANILINE
• 1-Iodoheptane
• DL-Mandelic acid
• 5-Bromo-3-nitropyridine-2-carbonitrile
• 4-Bromophenoxybenzene
• Iron(III) trifluoromethanesulfonate
• 2-CYANO-6-FLUOROBENZALDEHYDE
• 3-Cyano-4-fluorobenzaldehyde 97%,3-Cyano-4-fluorobenzaldehyde97%,3-CYANO-4-FLUOROBENZALDEHYDE
• 2-CYANO-4-FLUOROBENZALDEHYDE
• 4-CYANO-2-FLUOROBENZALDEHYDE
• Topotecan(Tpt)
• 5-CYANO-2-FLUOROBENZALDEHYDE
• 2-Cyano-5-fluorobenzaldehyde
• 3-Cyano-5-fluorobenzaldehyde
• 4-CYANO-3-FLUOROBENZALDEHYDE
• 2,4-DIFLUORO-3-FORMYLBENZONITRILE
• 5-CYANO-2-FLUOROBENZOIC ACID METHYL ESTER
• 5-CYANO-2-FLUOROBENZOIC ACID ETHYL ESTER