4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE Chemical Properties

Melting point:

26-30 °C(lit.)

Boiling point:

95 °C4 mm Hg(lit.)

Density 

1.662 g/mL at 25 °C(lit.)

refractive index 

1.4610 (estimate)

Flash point:

205 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

low melting crystals

color 

Colourless

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

BRN 

1956460

InChI

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

InChIKey

IHGSAQHSAGRWNI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

16184-89-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich

4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE Usage And Synthesis

Chemical Properties

Clear light yellow liquid

Uses

4?-Bromo-2,2,2-trifluoroacetophenone may be used in the preparation of carbonyl-bridged bithiazole derivatives. Also used as a reagent to synthesize MK-5046, a selective Bombesin receptor subtype-3 agonist used to treat obesity.

Synthesis

A. Synthesis of 1-(4-bromophenyl)-2,2,2-trifluoro-1-acetophenone 1,2-Dibromobenzene (6.0 g, 0.025 mol) was dissolved in 59 mL of anhydrous tetrahydrofuran in a flame-dried flask. The solution was cooled to -78 °C in a dry ice/acetone bath and n-butyllithium (2.56 M hexane solution, 9.8 mL, 0.025 mol) was slowly added dropwise, keeping the reaction temperature below -60 °C during the reaction. After addition, the reaction mixture was stirred at -78 °C for 1 hour. The solution was then added dropwise via cannula to a solution of ethyl trifluoroacetate (3.56 g, 0.0257 mol) in 36 mL of ether and cooled to -78 °C. After addition, the reaction mixture was stirred at -70 °C for 15 min and then gradually warmed to room temperature. The reaction mixture was partitioned between ether and saturated aqueous ammonium chloride solution, and the pH of the aqueous phase was adjusted to about pH = 2 by dropwise addition of 1 M HCl. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated to give 10 g (> 100%) of crude compound A, which was used without further purification for the next reaction.

References

[1] Patent: EP768305, 1997, A1

4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(16184-89-7)Related Product Information

• 3'-BROMO-2,2,2-TRIFLUOROACETOPHENONE
• 1-(4-BROMO-3-FLUORO-PHENYL)-2,2,2-TRIFLUORO-ETHANONE
• 1-Bromo-4-(2,2,2-trifluoroethyl)benzene
• Trifluoroacetophenone
• 4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE