367907
Sodium trifluoromethanesulfonate
98%
Synonym(s):
Sodium triflate, Trifluoromethanesulfonic acid sodium salt
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About This Item
Linear Formula:
CF3SO3Na
CAS Number:
Molecular Weight:
172.06
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3728797
Assay:
98%
Form:
solid
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
Related Categories
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:
It can be also used as supporting electrolyte in electrochemical O-glycosylation of primary alcohols with O-protected thioglycosides.
- 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.
signalword
Warning
hcodes
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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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)
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
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