4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE Chemical Properties

Melting point:

55 °C

Boiling point:

266.0±35.0 °C(Predicted)

Density 

1.621±0.06 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

color 

Pale yellow

CAS DataBase Reference

103962-10-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38-36

Safety Statements 

26-36/37/39

RIDADR 

1759

WGK Germany 

3

HazardClass 

CORROSIVE

HS Code 

2914500090

4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE Usage And Synthesis

Uses

2-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-one is an intermediate used to prepare aminothiazoles as therapeutic leads for prion diseases. It is also used in the synthesis of pyrrolidino-tetrahydroisoquinolines as potent dual H3 antagonist and serotonin transporter inhibitors.

Synthesis

General procedure for the synthesis of 2-bromo-1-[4-(trifluoromethoxy)phenyl]ethanone from 4'-(trifluoromethoxy)acetophenone: To a preheated (80 °C) stirred solution of copper(II) bromide (17.2 g, 77.2 mmol) in ethyl acetate (20 mL) was slowly added 4'-(trifluoromethoxy)acetophenone (8.7 g, 42.89 mmol) in a chloroform (10 mL) solution. The reaction mixture was stirred continuously at 80 °C for 4 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove solid impurities. The filtrate was subsequently concentrated under reduced pressure to give the crude product. The crude product was further purified by silica gel column chromatography with an eluent of 2-2.5% dichloromethane/hexane mixed solvent, resulting in the target compound 2-bromo-1-[4-(trifluoromethoxy)phenyl]ethanone (7 g, 58.0% yield) as an off-white solid. Its 1H NMR (400 MHz, CDCl3) data were as follows: δ 8.05 (d, J=8.0 Hz, 2H), 7.32 (d, J=8.8 Hz, 2H), 4.41 (s, 2H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 18, p. 7677 - 7702
[2] Patent: WO2018/165520, 2018, A1. Location in patent: Page/Page column 223
[3] Patent: WO2013/131408, 2013, A1. Location in patent: Page/Page column 128
[4] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 253 - 266
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1432 - 1435

4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE(103962-10-3)Related Product Information

• 4-(DIFLUOROMETHOXY)BENZALDEHYDE
• 4-METHOXYPHENETHYL BROMIDE
• 2-Bromo-4'-methoxyacetophenone
• 4'-(Trifluoromethoxy)acetophenone
• 4-(Trifluoromethoxy)benzaldehyde
• 2-Bromoacetophenone
• 4-(DIFLUOROMETHOXY)PHENACYL BROMIDE
• 4-Trifluoromethoxytoluene
• 4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE
• 4-(2-BROMOETHYL)PHENOL
• 4-(DIFLUOROMETHOXY)ACETOPHENONE
• 2-Bromo-4'-hydroxyacetophenone
• 2-Bromo-3'-(trifluoromethoxy)acetophenone
• 2-(TRIFLUOROMETHOXY)PHENACYL BROMIDE
• 2-Bromo-2'-(trifluoromethoxy)acetophenone
• 2-HYDROXY-5-(TRIFLUOROMETHOXY)PHENACYL BROMIDE
• 3-(TRIFLUOROMETHOXY)PHENACYL BROMIDE
• ETHYL 2-BROMO-3-(4-TRIFLUOROMETHOXYPHENYL)-3-OXO-PROPANOATE