8.21166
Trifluoromethanesulfonic acid
for synthesis
别名:
Trifluoromethanesulfonic acid, Triflic acid, TFMS
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关于此项目
经验公式（希尔记法）:
CHF3O3S
化学文摘社编号:
分子量:
150.08
UNSPSC Code:
12352106
EC Index Number:
216-087-5
NACRES:
NA.22
MDL number:
产品名称
Trifluoromethanesulfonic acid, for synthesis
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
grade
synthesis grade
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
Quality Level
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.
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.
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.
signalword
Danger
Hazard Classifications
Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3
target_organs
Respiratory system
存储类别
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
Trifluoromethanesulfonic acid and derivatives
R. D. Howells & J. D. Mc Cown JD
Chemical Reviews, 77, 69-69 (1977)
Highly efficient p-toluenesulfonic acid-catalyzed alcohol addition or hydration of unsymmetrical arylalkynes
Olivi N, et al.
Synlett, 2004, 2175-2179 (2004)
Solid Phase Peptide Synthesis, Pierce Chemical Company, Rockford, 1984.
J. Stewart, J. Young
Solid Phase Peptide Synthesis (1984)
Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol
Sagawa T, et al.
Molecular Catalysis, 111282-111282 (2020)
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)
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