2-Bromo-5-(trifluoromethyl)benzaldehyde Chemical Properties

Boiling point:

239.1±35.0 °C(Predicted)

Density 

1.677±0.06 g/cm3(Predicted)

refractive index 

1.511

storage temp. 

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

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Sensitive 

Air Sensitive

InChI

InChI=1S/C8H4BrF3O/c9-7-2-1-6(8(10,11)12)3-5(7)4-13/h1-4H

InChIKey

CSOBJYGHQOLWOD-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(C(F)(F)F)=CC=C1Br

CAS DataBase Reference

102684-91-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2913000090

2-Bromo-5-(trifluoromethyl)benzaldehyde Usage And Synthesis

Chemical Properties

Pale yellow liquid

Synthesis

To a solution of the 2-bromo-5-trifluoromethyl-benzonitrile (2.6 g, 10.4 mmol) in toluene (20 mL) at -78° C. was added diisobutylaluminium hydride (21 mL, 21 mmol, 1.0 M in toluene) cooled to -78° C. by cannula. The solution was stirred at -78 to -50° C. for 2 hours. Water (5 mL) was added slowly to the reaction and the reaction was allowed to warm up to room temperature. The mixture was adjusted to pH 10 with NaOH. The product was extracted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexanes/ether 90:10) to give 2-Bromo-5-(trifluoromethyl)benzaldehyde (2.0 g, 76 %) as a dark solid.

References

[1] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1442 - 1452
[2] Patent: US2007/21408, 2007, A1. Location in patent: Page/Page column 130-131
[3] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 483 - 487
[4] Patent: US2005/261310, 2005, A1. Location in patent: Page/Page column 24

2-Bromo-5-(trifluoromethyl)benzaldehyde(102684-91-3)Related Product Information

• 2-BROMO-5-(TRIFLUOROMETHYL)BENZOIC ACID
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• ethyl 2-bromo-5-(trifluoromethyl)benzoate
• 2-Bromo-5-(trifluoromethyl)benzaldehyde
• 2-bromo-5-(trifluoromethyl)benzamide
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• 3-Bromo-5-(trifluoromethyl)benzaldehyde oxime,3-Bromo-5-(trifluoromethyl)benzaldehyde oxime 98%
• 2-BROMO-3-(TRIFLUOROMETHYL)BENZALDEHYDE
• 3-Bromo-5-(trifluoromethyl)benzaldehyde97%,3-BROMO-5-(TRIFLUOROMETHYL)BENZALDEHYDE
• 4-BROMO-2-(TRIFLUOROMETHYL)BENZALDEHYDE
• 2-Bromo-5-(trifluoromethyl)benzaldehyde minimum
• 4-BROMO-3-TRIFLUOROMETHYL-BENZALDEHYDE
• 2-bromo-5-(trifluoromethyl)benzaldehyde 95%