2-Bromo-2'-fluoroacetophenone Chemical Properties

Melting point:

25-27

Boiling point:

83-85

Density 

1.574 g/mL at 25 °C

refractive index 

n20/D1.563

Flash point:

>110 °C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

Sensitive 

Lachrymatory

Stability:

Unstable in DMSO

CAS DataBase Reference

655-15-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

36/37/38-34

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3261 8 / PGIII

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory/Keep Cold

HazardClass 

LACHRYMATOR, CORROSIVE

HazardClass 

8

PackingGroup 

III

HS Code 

2914790090

2-Bromo-2'-fluoroacetophenone Usage And Synthesis

Chemical Properties

Liquid

Uses

A new class of acetophenone-based cinchona alkaloid-derived quaternary ammonium salts were prepared and evaluated as phase-transfer catalysts in the enantioselective alkylation of glycine imine ester.

Synthesis

General procedure for the synthesis of 2-bromo-2'-fluoroacetophenone from o-fluoroacetophenone: bromine (5.8 mL) was added slowly and dropwise to a solution of 1-(2-fluorophenyl)ethanone (15.1 g) in acetic acid (150 mL). The reaction mixture was stirred at room temperature for 2 h. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate, water and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford 2-bromo-2'-fluoroacetophenone (22.91 g, 97% yield) as a light yellow oil. The product was characterized by 1H-NMR (CDCl3): δ 4.53 (2H, d, J = 2.4 Hz), 7.13-7.20 (1H, m), 7.27-7.30 (1H, m), 7.54-7.61 (1H, m), 7.91-7.96 (1H, m).

References

[1] Patent: US2009/156642, 2009, A1. Location in patent: Page/Page column 40
[2] Patent: EP2196459, 2010, A1. Location in patent: Page/Page column 78
[3] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 20, p. 3763 - 3772
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582

2-Bromo-2'-fluoroacetophenone(655-15-2)Related Product Information

• 3-Nitroacetophenone
• Calcium bromide
• Ethidium bromide
• 4'-(Trifluoromethyl)acetophenone
• 4-Nitroacetophenone
• 1-(2,6-Difluorophenyl)ethan-1-one
• 2',4'-Difluoroacetophenone
• Trifluoroacetophenone
• Acetophenone
• 2',4'-Dichloroacetophenone
• 2-Fluorobenzyl cyanide
• 2'-Fluoroacetophenone
• Sodium bromate
• 4-Fluoroacetophenone
• 3'-Fluoroacetophenone
• 2-Bromoacetophenone
• 2-Bromo-2'-nitroacetophenone
• 4'-Bromoacetophenone