4-Fluoro-2-methylbenzaldehyde Chemical Properties

Boiling point:

87 14mm

Density 

1.144 g/mL at 25 °C

refractive index 

1.5260

Flash point:

82 °C

storage temp. 

Inert atmosphere,2-8°C

form 

clear liquid

color 

Colorless to Almost colorless

Sensitive 

Air Sensitive

CAS DataBase Reference

63082-45-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-36-39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29130000

4-Fluoro-2-methylbenzaldehyde Usage And Synthesis

Chemical Properties

Clear colorless to light yellow liquid

Uses

4-FLUORO-2-METHYLBENZALDEHYDE is a useful research chemical.

Synthesis

Example 1: This example illustrates the synthesis of 4-fluoro-2-methylbenzaldehyde (see Figure III, Scheme I). The procedure was as follows: 2-bromo-5-fluorotoluene (37.5 mL, 56.1 g, 297 mmol) was dissolved in 500 mL of anhydrous tetrahydrofuran (THF) and the solution was cooled to -78 °C. A hexane solution of 2.5 M butyllithium (119 mL, 297 mmol, 1.0 eq.) was slowly added over 35 min at -75 to -78 °C, followed by stirring of the reaction mixture at -78 °C for 20 min. Dry N,N-dimethylformamide (27.6 mL, 26.0 g, 356 mmol, 1.2 eq.) was added over 26 min at the same temperature range. After addition, the reaction solution was continued to be stirred at -78 °C for 60 min, and then slowly warmed to 15 °C, taking about 2 hours. An aqueous ammonium chloride solution (100 g, 15.9%) was added over 5 min at 15-20 °C. The reaction mixture was concentrated by fractional distillation (50-61°C fractions were collected, totaling 597 mL) and the distillate layer was separated. The aqueous layer was extracted three times with methyl tert-butyl ether (MTBE, 25 mL x 3). The organic layers were combined, washed with 50 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered and fractionated again (boiling point 54-62 °C) to give 59.3 g of yellow oil. The crude product was further purified by fractional distillation under reduced pressure (boiling point 60-62 °C, pressure 1.6-2.0 mmHg) to finally obtain 28.041 g (68.4% yield) of the target product 4-fluoro-2-methylbenzaldehyde in the form of a colorless oil.

Purification Methods

The aldehyde has been purified by gas chromatography and should be kept under N2 as it readily oxidizes in air [Burgess et al. Aust J Chem 30 543 1977].

References

[1] Patent: WO2004/110996, 2004, A1. Location in patent: Page/Page column 17-18
[2] Patent: WO2005/37763, 2005, A1. Location in patent: Page/Page column 82
[3] Patent: US2006/14959, 2006, A1. Location in patent: Page/Page column 10
[4] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
[5] Patent: EP1787991, 2007, A1. Location in patent: Page/Page column 45

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