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8.21166

Trifluoromethanesulfonic acid

for synthesis

Synonym(s):

Trifluoromethanesulfonic acid, Triflic acid, TFMS

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About This Item

Empirical Formula (Hill Notation):
CHF3O3S
CAS Number:
1493-13-6
Molecular Weight:
150.08
UNSPSC Code:
12352106
EC Index Number:
216-087-5
NACRES:
NA.22
MDL number:
MFCD00007514
Form:
liquid
Grade:
synthesis grade
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grade

synthesis grade

Quality Level

200

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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pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

wgk

WGK 1

Storage Class

8B - Non-combustible corrosive hazardous materials

Certificates of Analysis (COA)

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Global Trade Item Number

SKUGTIN
821166100004027269992668
821166002504022536475097
821166010004022536475103