2-CHLORO-3-(TRIFLUOROMETHYL)BENZALDEHYDE Chemical Properties

Melting point:

37-43 °C (lit.)

Boiling point:

216.6±35.0 °C(Predicted)

Density 

1.423±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

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

form 

Crystals or Powder

color 

White to off-white

Sensitive 

Air Sensitive

BRN 

3543607

CAS DataBase Reference

93118-03-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29122900

MSDS

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

2-CHLORO-3-(TRIFLUOROMETHYL)BENZALDEHYDE Usage And Synthesis

Uses

2-Chloro-3-(trifluoromethyl)benzaldehyde can be used as an organic synthesis intermediate, which can be prepared by reacting 2-trifluoromethyl-chlorobenzene with n-butyllithium. It can be used to prepare the pharmaceutical intermediate (2-chloro-3-trifluoromethylbenzyl)cyclopropylamine.

General Description

4-Chloro-3-(trifluoromethyl)benzaldehyde is a substituted benzaldehyde.

Synthesis

The general procedure for the synthesis of 2-chloro-3-(trifluoromethyl)benzaldehyde from N,N-dimethylformamide was as follows: n-butyllithium (1.6 M hexane solution, 173 mL, 277 mmol) was added dropwise to the reaction system at -70 °C. Subsequently, a tetrahydrofuran (500 mL) solution of 2-trifluoromethylchlorobenzene (50.0 g, 277 mmol) was slowly added. The reaction temperature was maintained at -70°C and the reaction mixture was stirred for 2 hours. Then, a tetrahydrofuran (100 mL) solution of N,N-dimethylformamide (21.3 mL, 277 mmol) was added. The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched by the addition of water (200 mL) and the mixture was extracted with ether (2 x 200 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by fast column chromatography (eluent: heptane/ethyl acetate=20:1) to afford the target product 2-chloro-3-(trifluoromethyl)benzaldehyde (37.4 g, 65% yield). Analyzed by liquid chromatography-mass spectrometry: retention time t R = 0.96 min.

References

[1] Patent: WO2006/21402, 2006, A1. Location in patent: Page/Page column 42

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