NaOTf Chemical Properties

Melting point:

253-255 °C (lit.)

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

White to off-white

Water Solubility 

soluble

Sensitive 

Hygroscopic

Hydrolytic Sensitivity

0: forms stable aqueous solutions

BRN 

3728797

InChI

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

InChIKey

KKVTYAVXTDIPAP-UHFFFAOYSA-M

SMILES

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

CAS DataBase Reference

2926-30-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39

WGK Germany 

3

F 

3-10

Hazard Note 

Corrosive

TSCA 

No

HS Code 

29049090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

NaOTf Usage And Synthesis

Description

Sodium trifluoromethanesulfonate (NaOTf) is commonly known as trifluoromethanesulfonic acid or TFMS. Possessing unique properties, TFMS is water-soluble, anionic, and boasts a range of valuable attributes. As a colorless, odorless, and non-toxic substance, TFMS finds widespread use as a reagent in organic synthesis, a catalyst in industrial applications, and a buffer in various biochemical experiments. In scientific research, TFMS stands out due to its robust acidity, enabling it to act as a potent catalyst in organic synthesis. Additionally, it effectively serves as a reliable buffer at pH levels, ensuring precise pH maintenance in biochemical experiments. As an anionic compound, TFMS functions as a strong acid in solution, facilitating the donation of protons to other molecules, thus reducing the pH.

Chemical Properties

White to off-white powder

Uses

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.

Uses

NaOTf is used in the preparation of N-fluoro-2-methylpyridinium triflate by reaction with dinitrogen difluoride as a reagent. It is also used as a chaotropic mobile phase additive in reversed-phase liquid chromatography (RP-LC).

Preparation

NaOTf is prepared by adding a slight excess of sodium sulfate to an aqueous solution of barium trifluoromethanesulfonate. The reaction mixture is stirred for several minutes and allowed to stand for one day, and the white precipitate of barium sulfate is removed by filtration. The clear filtrate is evaporated to dryness, and the solid product is recrystallized from dry acetone. The salt is dried under vacuum at 110°C.1 Barium trifluoromethanesulfonate can be easily prepared from aqueous trifluoromethanesulfonic acid and barium carbonate. Other methods include the preparation of sodium trifluoromethane sulfonate from sodium dithionite and bromotrifluoromethane and its oxidation to sodium trifluoromethane sulfonate using hydrogen peroxide.

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.

Battery Materials

Hard carbon-based sodium-ion batteries (HC-based SIBs)  have poor performance at low temperatures. Jidao Li and colleagues^[1] propose an anion-inverted coordination electrolyte strategy using sodium trifluoromethanesulfonate (NaOTf). This optimized electrolyte enhances ionic conductivity, interfacial stability, and low-temperature performance.

Solubility in organics

soluble in water, alcohol, acetonitrile, N,N-dimethylformamide, and most highly polar organic solvents.

References

[1] Li, J., Long, J., Gong, H., Zhou, S., Wang, J., Jiang, Z., Huang, S., Zhou, Q., Wang, F., Shi, J., Zhang, Y., Bai, Z., & Tang, Y. (2026). Anion-inverted coordination: An "ice-breaking" ether electrolytes for low temperature sodium battery. Chemical Engineering Journal, 538, 176555. https://doi.org/10.1016/j.cej.2026.176555

NaOTf(2926-30-9)Related Product Information

• 2-(Trifluoromethyl)benzoic acid
• Formaldehyde sodium bisulfite
• Sodium formate
• Sodium acetate
• YTTERBIUM(III) TRIFLUOROMETHANESULFONATE HYDRATE
• Sodium hydroxide
• COPPER(II) TRIFLUOROMETHANESULFONATE
• Sodium bicarbonate
• Trifluoromethanesulfonic acid
• Trifluoromethanesulfonic anhydride
• Pefloxacin mesylate
• Sodium carbonate
• TRIFLUOROMETHANESULFONYL FLUORIDE
• Sodium gluconate
• Levofloxacin Methylate
• Lithium trifluoromethanesulfonate
• 3-Aminobenzotrifluoride
• Sodium benzoate