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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 Segment

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Deleterious substance

pdsc

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

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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