8.21166

Trifluoromethanesulfonic acid

for synthesis

• Synonym(s): Trifluoromethanesulfonic acid, Triflic acid, TFMS
• Empirical Formula (Hill Notation): CHF₃O₃S
• CAS Number: 1493-13-6
• Molecular Weight: 150.08
• MDL number: MFCD00007514
• UNSPSC Code: 12352106
• EC Index Number: 216-087-5
• NACRES: NA.22

Properties

• vapor pressure: 10 hPa ( 55 °C)
• Quality Level: 200
• form: liquid
• potency: 1605 mg/kg LD₅₀, oral (Rat); >2000 mg/kg LD₅₀, skin (Rat)
• pH: <1 ( in H₂O)
• bp: 162 °C/1013 hPa
• density: 1.71 g/cm³ at 20 °C
• storage temp.: 2-30°C
• InChI: 1S/2CHF3O3S.Ba/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2
• InChI key: DXJURUJRANOYMX-UHFFFAOYSA-L

Description

General description

Trifluoromethanesulfonic acid (also known as Triflic acid, TFMSA or TfOH) is an organic acid that is commonly used as a reagent in organic synthesis due to its strong Bronsted acidity, finding applications in catalysis, N-protection, dehydration, activation, and addition reactions.^, TFMSA is also used for global deprotection and cleavage in Boc SPPS.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Boc SPPS

Literature references:
^[1] L. R. Subramanian, et al. (2001) Encyclopedia of Reagents for Organic Synthesis.
^[2] R. D. Howells & J. D. Mc Cown JD (1977) Chem. Rev., 77, 69.
^[3] J. Stewart, J. Young in “Solid Phase Peptide Synthesis”, Pierce Chemical Company, Rockford, 1984.

Application

Recent applications of trifluoromethanesulfonic acid include:

• A dehydrating agent for the conversion of secondary alcohols to alkene, or the preparation of anhydrides from carboxylic acids.
• An acid catalyst in the synthesis of carbohydrates and glycosides.
• An activating agent for the activation of carboxylic acids and can be used for the synthesis of carboxylic acid derivatives such as esters, amides, and anhydrides.

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H290 - H302 - H314 - H335
• pcodes: P234 - P261 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 8A - Combustible, corrosive hazardous materials
• wgk_germany: WGK 1
• flash_point_f: 332.1 °F - Pensky-Martens closed cup
• flash_point_c: > 166.7 °C - Pensky-Martens closed cup