2-Bromoethyl trifluoromethanesulphonate Chemical Properties

Boiling point:

230 °C

Density 

1.903±0.06 g/cm3(Predicted)

storage temp. 

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

form 

liquid

color 

clear

InChI

InChI=1S/C3H4BrF3O3S/c4-1-2-10-11(8,9)3(5,6)7/h1-2H2

InChIKey

KENPFZUYYWVXNW-UHFFFAOYSA-N

SMILES

C(F)(F)(F)S(OCCBr)(=O)=O

Safety Information

HS Code 

2904990090

2-Bromoethyl trifluoromethanesulphonate Usage And Synthesis

Synthesis

Pyridine (1.74 kg, 22.01 mol, 1.10 eq.) was dissolved in dichloromethane (20 L) under nitrogen protection and the solution was cooled to -20 °C. Subsequently, trifluoromethanesulfonic anhydride (5.87 kg, 20.81 mol, 1.04 eq.) was added slowly and dropwise. The reaction system was maintained at -20 °C with stirring for 0.5 hours. Then, 2-bromoethanol (2.50 kg, 20.01 mol, 1.0 eq.) was slowly added dropwise and the reaction temperature was ensured to be maintained below 0 °C and stirring was continued for 1.0 hour. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether: ethyl acetate = 5:1) to confirm the completion of the reaction. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated. Petroleum ether (15 L) was added to the concentrate, the precipitated solid was filtered, and the filtrate was concentrated again to obtain the target product (4.80 kg, 93.33% yield) of trifluoromethanesulfonic acid (2-bromoethyl) ester as a dark yellow oil.

References

[1] Patent: CN107955019, 2018, A. Location in patent: Paragraph 0098; 0099; 0100
[2] Tetrahedron, 1999, vol. 55, # 35, p. 10659 - 10672
[3] Patent: WO2009/153554, 2009, A1. Location in patent: Page/Page column 62
[4] Angewandte Chemie - International Edition, 2008, vol. 47, # 20, p. 3784 - 3786
[5] Patent: WO2017/147410, 2017, A1. Location in patent: Page/Page column 180

2-Bromoethyl trifluoromethanesulphonate(103935-47-3)Related Product Information

• Nickel(II) Trifluoromethanesulfonate
• Trifluoromethanesulfonic acid
• SAMARIUM(III) TRIFLUOROMETHANESULFONATE
• YTTRIUM(III) TRIFLUOROMETHANESULFONATE
• 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE
• Iron(III) trifluoromethanesulfonate
• Lanthanum trifluoromethanesulfonate
• Aluminum trifluoromethanesulfonate
• Sodium trifluoroacetate
• 2,2-DIFLUOROETHYL TRIFLUOROMETHANESULFONATE
• Scandium trifluoromethanesulfonate
• PALLADIUM(II) TRIFLUOROACETATE
• Methyl trifluoromethanesulfonate
• Trifluoromethanesulfonic anhydride
• Trimethylsilyl trifluoromethanesulfonate
• Sulfurous Acid
• 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE
• Methanesulfonic acid, trifluoro-, 2-methoxy-5-nitrophenyl ester