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367907

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:
3728797
MDL number:
MFCD00061607
UNSPSC Code:
12352302
PubChem Substance ID:
24862862
NACRES:
NA.22

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV9410
0000256514
0000240903
MKCT4412
0000256514

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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
Sodium 1, 1, 1-Trifluoromethanesulfonate
Surya PGK and Mathew T
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 132(34), 12150-12154 (2001)
Silver-catalyzed late-stage fluorination
Tang P, et al.
Journal of the American Chemical Society, 132(34), 12150-12154 (2010)
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)
Chiwon Kang et al.
Materials (Basel, Switzerland), 12(8) (2019-04-26)
High theoretical capacity and low-cost copper sulfide (CuxS)-based anodes have gained great attention for advanced sodium-ion batteries (SIBs). However, their practical application may be hindered due to their unstable cycling performance and problems with the dissolution of sodium sulfides (NaxS)
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