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Sigma-Aldrich

Sodium trifluoromethanesulfonate

98%

Synonym(s):

Sodium triflate, Trifluoromethanesulfonic acid sodium salt

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About This Item

Linear Formula:
CF3SO3Na
CAS Number:
2926-30-9
Molecular Weight:
172.06
Beilstein/REAXYS Number:
3728797
MDL number:
MFCD00061607
UNSPSC Code:
12352302
PubChem Substance ID:
24862862
NACRES:
NA.22

assay

98%

form

solid

mp

253-255 °C (lit.)

SMILES string

[Na+].[O-]S(=O)(=O)C(F)(F)F

InChI

1S/CHF3O3S.Na/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1

InChI key

XGPOMXSYOKFBHS-UHFFFAOYSA-M

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General description

Sodium trifluoromethanesulfonate (Sodium triflate or NaOTf) is an efficient catalyst as well as a reagent in many organic reactions. The prominent application includes catalytic asymmetric Mannich-type reactions, Mannich-type reactions in water, and Diels-Alder reactions.It is also used as an electrolyte in batteries.

Application

Sodium trifluoromethanesulfonate can be employed as a reagent for the preparation of:
  • Aryl fluorides via silver-catalyzed fluorination of arylstannanes.
  • Ionic liquids such as N, N -dialkylpyrrolidinium triflate, N,N-dialkylimidazolium triflate, and N-alkylpyridinium triflate.

It can be also used as supporting electrolyte in electrochemical O-glycosylation of primary alcohols with O-protected thioglycosides.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Bing Sun et al.
Advanced materials (Deerfield Beach, Fla.), 29(48) (2017-04-05)
As a new family member of room-temperature aprotic metal-O
Electrochemical O-glycosylation using thioglycosides as glycosyl donors in the presence of a catalytic amount of sodium trifluoromethanesulfonate as a supporting electrolyte
Tanaka N, et al.
Tetrahedron Letters, 48(41), 7383-7387 (2007)
Chenjuan Liu et al.
ACS applied materials & interfaces, 10(16), 13534-13541 (2018-04-05)
Na-O2 batteries are regarded as promising candidates for energy storage. They have higher energy efficiency, rate capability, and chemical reversibility than Li-O2 batteries; in addition, sodium is cheaper and more abundant compared to lithium. However, inconsistent observations and instability of
Risa Iima et al.
AAPS PharmSciTech, 19(6), 2679-2686 (2018-06-27)
We developed carriers of a 19F magnetic resonance imaging (19F MRI) agent, capable of responding to the temperature difference for cancer diagnosis. The carriers were based on high melting point (mp) neutral lipids, namely, tripalmitin (TPT) and tristearin (TSR) and
Laura Mortara et al.
Langmuir : the ACS journal of surfaces and colloids, 34(37), 11049-11057 (2018-08-22)
Zwitterionic micelles adsorb anions and several techniques were used to determine the specificity of this interaction. Although at a lower intensity, this adsorption can be compared to those observed in cationic micelles, which showed that interfacial dehydration is a fundamental
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