2,2,2-Trifluoroethyl trifluoromethanesulfonate Chemical Properties

Boiling point:

89-91°C

Density 

1,61 g/cm³

refractive index 

1.3037

RTECS 

PB2775000

Flash point:

>110°(230°F)

storage temp. 

2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

color 

Colorless to yellow

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C3H2F6O3S/c4-2(5,6)1-12-13(10,11)3(7,8)9/h1H2

InChIKey

RTMMSCJWQYWMNK-UHFFFAOYSA-N

SMILES

C(F)(F)(F)S(OCC(F)(F)F)(=O)=O

CAS DataBase Reference

6226-25-1(CAS DataBase Reference)

EPA Substance Registry System

Methanesulfonic acid, trifluoro-, 2,2,2-trifluoroethyl ester (6226-25-1)

Safety Information

Hazard Codes 

Xi,T,C

Risk Statements 

36/37/38-34-23/25

Safety Statements 

26-36/37/39-45

RIDADR 

3265

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

TOXIC, CORROSIVE

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

29055900

2,2,2-Trifluoroethyl trifluoromethanesulfonate Usage And Synthesis

Uses

A fluorine-containing alkyl alkanesulfonate with cyctotoxity towards cultured leukemia L1210 cells.

Uses

2,2,2-Trifluoroethyl trifluoromethanesulfonate is a powerful trifluoroethylating agent which is useful for synthesis of fluorinated amino acids. It is used as a reagent in thenantioselective preparation of cyclic N-aryl hydroxamic acids via phase-transfer catalyzed alkylation of nitrobenzyl bromides to give nirophenylalanines.

Uses

Reagent used in thenantioselective preparation of cyclic N-aryl hydroxamic acids via phase-transfer catalyzed alkylation of nitrobenzyl bromides to give nirophenylalanines

Synthesis

In a 100-ml flask equipped with a stirrer, a thermometer, a nitrogen introducing pipe, and a condenser, 50 ml (0.297 mol) of trifluoromethane sulfonic anhydride and 25 ml (0.342 moles) of 2,2,2-trifluoroethanol were placed at room temperature and stirred for 30 minutes in a nitrogen atmosphere, followed by reflux for 3 hours. After distillation, 50.3 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate was obtained in a yield of 73%.

References

[1] Patent: US2014/249162, 2014, A1. Location in patent: Paragraph 0423; 0424; 0425
[2] Patent: EP2781519, 2014, A1. Location in patent: Paragraph 0404; 0405; 0406
[3] Tetrahedron, 1988, vol. 44, # 17, p. 5375 - 5387
[4] Journal of Organic Chemistry, 1984, vol. 49, # 12, p. 2258 - 2273
[5] Journal of Fluorine Chemistry, 2016, vol. 192, p. 131 - 140

2,2,2-Trifluoroethyl trifluoromethanesulfonate(6226-25-1)Related Product Information

• Trifluoromethanesulfonic acid
• DIBUTYLBORON TRIFLUOROMETHANESULFONATE
• YTTERBIUM(III) TRIFLUOROMETHANESULFONATE HYDRATE
• COPPER(II) TRIFLUOROMETHANESULFONATE
• BUPIRIMATE
• Lithium trifluoromethanesulfonate
• FLUOROSULFONIC ACID
• Sodium isethionate
• Sodium trifluoromethanesulfonate
• Levofloxacin Methylate
• Trifluoromethanesulfonic anhydride
• Pefloxacin mesylate
• Ethyl methanesulfonate
• Methanesulfonic acid
• Methyl trifluoromethanesulfonate
• Trimethylsilyl trifluoromethanesulfonate
• Ethyl trifluoromethanesulfonate
• HEXAFLUOROISOPROPYL TRIFLUOROMETHANESULFONATE