2,6-Difluorobenzaldehyde Chemical Properties

Melting point:

15-17 °C (lit.)

Boiling point:

82-84 °C/15 mmHg (lit.)

Density 

1.317 g/mL at 25 °C (lit.)

vapor pressure 

40.1-900hPa at 94.5-189℃

refractive index 

n20/D 1.502(lit.)

Flash point:

164 °F

storage temp. 

2-8°C

form 

Liquid

Specific Gravity

1.317

color 

Clear light yellow to bright yellow

Sensitive 

Air Sensitive

BRN 

1935273

InChIKey

SOWRUJSGHKNOKN-UHFFFAOYSA-N

LogP

1.46 at 25℃ and pH2

Surface tension

73.1mN/m at 1g/L and 20℃

CAS DataBase Reference

437-81-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39-36/37

WGK Germany 

2

F 

10-23

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

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

2,6-Difluorobenzaldehyde Usage And Synthesis

Chemical Properties

clear light yellow to bright yellow liquid

Uses

2,6-Difluorobenzaldehyde can be used as a reactant to synthesize:

• 5-Cyano-6-(2,6-difluorophenyl)-5,6-dihydro-2-thiouracil via one-pot cyclocondensation reaction with ethyl cyanoacetate and thiourea.
• 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazole by reacting with 1,2-phenylenediamine in the presence of a catalytic amount of p-toluenesulfonic acid.
• (3E)-4-(2,6-Difluorophenyl)-3-buten-2-one by Wittig olefination reaction with acetylmethylidenetriphenyl phosphorane.
• Methyl 4-fluorobenzo[b]thiophene-2-carboxylate by treating with methyl thioglycolate in the presence of K₂CO₃.

Synthesis

The general procedure for the synthesis of 2,6-dichlorobenzaldehyde from 2,6-dichlorobenzaldehyde was as follows: first, 34.8 g (0.6 mol) of potassium fluoride (KF) was dissolved in 250 mL of cyclobutanesulfone under nitrogen protection and stirred at 100 °C for 2 h. The water was removed by azeotropic distillation. Subsequently, 20 g (0.11 mol) of 2,6-dichlorobenzaldehyde and 2.8 g (6.68 mmol) of tetraphenylphosphonium bromide were added to this anhydrous mixture and the reaction mixture was heated to 180 °C and kept overnight. Upon completion of the reaction, the solid product was washed with ethyl acetate and the solvent was removed by aqueous pressure evaporation. Finally, the target product 2,6-difluorobenzaldehyde was purified by vacuum evaporation (24 mbar, 85-86 °C) in 77% yield.

References

[1] Patent: WO2016/102207, 2016, A1. Location in patent: Page/Page column 32
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Chemistry Letters, 1988, # 9, p. 1355 - 1358
[4] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2720 - 2725
[5] Patent: US6103659, 2000, A

2,6-Difluorobenzaldehyde(437-81-0)Related Product Information

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