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Trifluoromethanesulfonic acid

for synthesis

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Synonym(s):
Trifluoromethanesulfonic acid, Triflic acid, TFMS
Empirical Formula (Hill Notation):
CHF3O3S
CAS Number:
Molecular Weight:
150.08
MDL number:
EC Index Number:
216-087-5

vapor pressure

10 hPa ( 55 °C)

Quality Level

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

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This Item
3478171585348.18035
form

liquid

form

liquid

form

liquid

form

liquid

pH

<1 ( in H2O)

pH

-

pH

-

pH

-

bp

162 °C/1013 hPa

bp

162 °C (lit.)

bp

162 °C (lit.)

bp

99 °C/1013 hPa

density

1.71 g/cm3 at 20 °C

density

1.696 g/mL at 25 °C (lit.)

density

1.696 g/mL at 25 °C (lit.)

density

1.49 g/cm3 at 20 °C

storage temp.

2-30°C

storage temp.

-

storage temp.

-

storage temp.

2-30°C

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

Signal Word

Danger

Hazard Statements

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


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Trifluoromethanesulfonic acid and derivatives
R. D. Howells & J. D. Mc Cown JD
Chemical Reviews, 77, 69-69 (1977)
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Sagawa T, et al.
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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)
L. R. Subramanian, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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