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Merck

8.21166

Trifluoromethanesulfonic acid

for synthesis

Synonyme(s) :

Trifluoromethanesulfonic acid, Triflic acid, TFMS

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A propos de cet article

Formule empirique (notation de Hill) :
CHF3O3S
Numéro CAS:
Poids moléculaire :
150.08
UNSPSC Code:
12352106
EC Index Number:
216-087-5
NACRES:
NA.22
MDL number:
Form:
liquid
Grade:
synthesis grade
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grade

synthesis grade

Quality Level

vapor pressure

10 hPa ( 55 °C)

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

SMILES string

[Ba+2].FC(F)(F)[S](=O)(=O)[O-].FC(F)(F)[S](=O)(=O)[O-]

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

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.


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Danger

Hazard Classifications

Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Classe de stockage

8B - Non-combustible corrosive hazardous materials

wgk

WGK 1



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Trifluoromethanesulfonic acid and derivatives
R. D. Howells & J. D. Mc Cown JD
Chemical Reviews, 77, 69-69 (1977)
Solid Phase Peptide Synthesis, Pierce Chemical Company, Rockford, 1984.
J. Stewart, J. Young
Solid Phase Peptide Synthesis (1984)
Highly efficient p-toluenesulfonic acid-catalyzed alcohol addition or hydration of unsymmetrical arylalkynes
Olivi N, et al.
Synlett, 2004, 2175-2179 (2004)