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8.21166

Sigma-Aldrich

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
MDL number:
MFCD00007514
UNSPSC Code:
12352106
EC Index Number:
216-087-5
NACRES:
NA.22

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

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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H290 - H302 - H314 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

332.1 °F - Pensky-Martens closed cup

Flash Point(C)

> 166.7 °C - Pensky-Martens closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1,2-Cis Selective Glycosylation with Glycosyl Fluoride by Using a Catalytic Amount of Trifluoromethanesulfonic Acid (TfOH) in the Coexistence of Molecular Sieve 5? (MS5?)
Jona H, et al.
Chemistry Letters (Jpn), 29, 1278-1279 (2000)
Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol
Sagawa T, et al.
Molecular Catalysis, 111282-111282 (2020)
L. R. Subramanian, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
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