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ChemicalBook--->CAS DataBase List--->103935-47-3

103935-47-3

103935-47-3 Structure

103935-47-3 Structure
IdentificationBack Directory
[Name]

2-Bromoethyl trifluoromethanesulphonate
[CAS]

103935-47-3
[Synonyms]

2-Bromoethyl triflate
2-broMoethyl trifluoroMethanesulfonate
2-Bromoethyl trifluoromethanesulphonate
Trifluoro-methanesulfonic acid 2-bromo-ethyl ester
Methanesulfonic acid, trifluoro-, 2-broMoethyl ester
1,1,1-TrifluoroMethanesulfonic acid 2-broMo-ethyl ester
Methanesulfonic acid, 1,1,1-trifluoro-, 2-bromoethyl ester
[Molecular Formula]

C3H4BrF3O3S
[MDL Number]

MFCD11656439
[MOL File]

103935-47-3.mol
[Molecular Weight]

257.03
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]


GHS05,GHS06
[Signal word ]

Danger
[Hazard statements ]

H301+H311+H331-H314
[Precautionary statements ]

P261-P280-P305+P351+P338-P310
[HS Code ]

2904990090
Spectrum DetailBack Directory
[Spectrum Detail]

2-Bromoethyl trifluoromethanesulphonate(103935-47-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

Trifluoromethanesulfonic anhydride

358-23-6

2-Bromoethanol

540-51-2

2-Bromoethyl trifluoromethanesulphonate

103935-47-3

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
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