All Photos(3)
Synonym(s):
Sodium triflate, Trifluoromethanesulfonic acid sodium salt
Linear Formula:
CF3SO3Na
CAS Number:
Molecular Weight:
172.06
Beilstein:
3728797
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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:
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
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)
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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
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)
Willem Delabie et al.
Transfusion, 60(1), 165-174 (2019-10-28)
Supplementation of the nicotinamide adenine dinucleotide (NAD) precursor nicotinamide riboside (NR) has recently been shown to increase life-span of cells, tissues, and entire organisms. [Correction added on 13 December 2019, after first online publication: In the preceding sentence, "adenine nicotinamide"
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