2-CHLORO-3,6-DIFLUOROBENZALDEHYDE Chemical Properties

Melting point:

46-50 °C (lit.)

Boiling point:

206.4±35.0℃ (760 Torr)

Density 

1.453±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

230 °F

storage temp. 

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

Appearance

White to off-white Solid

Sensitive 

Air Sensitive

CAS DataBase Reference

261762-39-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

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

2-CHLORO-3,6-DIFLUOROBENZALDEHYDE Usage And Synthesis

Uses

2-Chloro-3,6-difluorobenzaldehyde is an aldehyde derivative that can be used as a pharmaceutical intermediate to prepare the downstream product 2-chloro-3,6-difluorobenzonitrile.

General Description

2-Chloro-3,6-difluorobenzaldehyde is a trisubstituted benzaldehyde. Fourier-transform, laser Raman (in the range of 3500-50cm^-1) and infrared (in the range of 4000-400cm^-1) spectral analyses of 2-chloro-3,6-difluorobenzaldehyde have been reported.

Synthesis

Example 152A Synthesis of 2-chloro-3,6-difluorobenzaldehyde: 2-chloro-1,4-difluorobenzene (1.78 g, 12.0 mmol) was dissolved in tetrahydrofuran (50 mL) and the solution was cooled to -78°C. Lithium diisopropylammonium (1.8 M in tetrahydrofuran, 7.3 mL, 13.2 mmol) was added slowly with stirring. The reaction temperature was maintained at -78 °C and stirring was continued for 30 min. Subsequently, N,N-dimethylformamide (1.05 g, 14.4 mmol) was added and stirring was continued at the same temperature for 15 min. After the reaction was completed, acetic acid (3 mL) and water (100 mL) were added and the mixture was gradually warmed up to room temperature. Extraction was carried out with ethyl acetate and the organic phases were combined and washed sequentially with 1 M hydrochloric acid solution and saturated saline. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-chloro-3,6-difluorobenzaldehyde (1.51 g, 71% yield). The product was analyzed by GC-MS (Method 1G): retention time Rt = 3.25 min, mass spectrum (ESI positive ion mode): m/z = 177 [M + H]+.

References

[1] Patent: WO2015/67549, 2015, A1. Location in patent: Page/Page column 143
[2] Patent: US2015/126449, 2015, A1. Location in patent: Paragraph 0803 - 0806

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