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Merck
CN

367907

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
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24862862
MDL number:
MFCD00061607
Beilstein/REAXYS Number:
3728797
Assay:
98%
Form:
solid

Key Documents

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Product Name

Sodium trifluoromethanesulfonate, 98%

InChI

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

SMILES string

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

InChI key

XGPOMXSYOKFBHS-UHFFFAOYSA-M

assay

98%

form

solid

mp

253-255 °C (lit.)

functional group

fluoro
triflate

Quality Level

100

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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.

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.

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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000511195
0000511200
0000511200
0000511195
MKCX5299

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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)
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
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)
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
Silver-catalyzed late-stage fluorination
Tang P, et al.
Journal of the American Chemical Society, 132(34), 12150-12154 (2010)
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