4-(DIFLUOROMETHOXY)BENZALDEHYDE Chemical Properties

Boiling point:

222 °C (lit.)

Density 

1.302 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.503(lit.)

Flash point:

228 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow

λmax

256nm(EtOH)(lit.)

Sensitive 

Air Sensitive

BRN 

3049286

CAS DataBase Reference

73960-07-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

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

4-(DIFLUOROMETHOXY)BENZALDEHYDE Usage And Synthesis

Chemical Properties

light yellow liquid

Uses

4-(Difluoromethoxy)benzaldehyde may be used for the preparation of 4-(4-difluoro-methoxy-phen-yl)-1,2,3,4,5,6,7,8-octa-hydro-quinazoline-2,5-dione, via one-pot three-component reaction with cyclo-hexane-1,3-dione and urea.

General Description

4-(Difluoromethoxy)benzaldehyde is a p-difluoromethoxy substituted benzaldehyde.

Synthesis

Example 1 Synthesis of 4-(difluoromethoxy)benzaldehyde: In a 1 L four-necked round-bottomed flask equipped with a thermometer, reflux condenser, mechanical stirrer, and gas introduction tube, 50 g (0.41 mol) of p-hydroxybenzaldehyde and 400 mL of isopropanol were added. After stirring the mixture for 20 minutes, 120 mL of a 120 mL aqueous solution containing 5 g of 18-crown-6 ether and 106.3 g (2.665 mol) of sodium hydroxide was slowly added dropwise. After the dropwise addition was completed, stirring was continued for 30 minutes and the mixture was subsequently heated to 65°C. Chlorodifluoromethane was slowly passed through the gas introduction tube over a period of 5-6 hours and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to 15 °C and 400 mL of water was added to quench the reaction. The reaction mixture was extracted three times with ether (3 x 300 mL). The organic layers were combined, washed with water to pH=7 and dried over anhydrous magnesium sulfate. The ether was removed by rotary evaporation and the residue was distilled under reduced pressure to collect the 85-87 °C/10 mmHg fraction to give 4-(difluoromethoxy)benzaldehyde in 95% yield.1H-NMR (ppm) δ: 9.87 (1H, s, -CHO); 7.70 (2H, m, 2,6-ArH); 7.36 (1H, t, J2H-F = 68 Hz, - CHF2); 6.96 (2H, m, 3,5-ArH).

References

[1] Patent: US2008/306027, 2008, A1. Location in patent: Page/Page column 7-8
[2] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 8.1, p. 1317 - 1324
[3] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 8, p. 1652 - 1660
[4] Journal of Fluorine Chemistry, 1988, vol. 41, p. 247 - 262

4-(DIFLUOROMETHOXY)BENZALDEHYDE(73960-07-3)Related Product Information

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