Skip to Content
MilliporeSigma
All Photos(3)

Documents

367907

Sigma-Aldrich

Sodium trifluoromethanesulfonate

98%

Synonym(s):

Sodium triflate, Trifluoromethanesulfonic acid sodium salt

Sign Into View Organizational & Contract Pricing
All Photos(3)

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

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

Looking for similar products? Visit Product Comparison Guide

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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)
Studies on ionic liquid based nanocomposite gel polymer electrolyte and its application in sodium battery
K Mishra, et al.
Materials Science and Engineering, B, 267, 115098-115098 (2021)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service