2-Bromoethyl trifluoromethanesulphonate

2-Bromoethyl trifluoromethanesulphonate Property

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

HS Code 

2904990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

2-Bromoethyl trifluoromethanesulphonate Chemical Properties,Usage,Production

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