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Merck
CN

8.21166

Sigma-Aldrich

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:
1493-13-6
分子量:
150.08
MDL编号:
MFCD00007514
UNSPSC代码:
12352106
EC索引号:
216-087-5
NACRES:
NA.22

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等级

synthesis grade

质量水平

200

蒸汽压

10 hPa ( 55 °C)

表单

liquid

效能

1605 mg/kg LD50, oral (Rat)
>2000 mg/kg LD50, skin (Rat)

pH值（酸碱度）

<1 ( in H2O)

沸点

162 °C/1013 hPa

密度

1.71 g/cm3 at 20 °C

储存温度

2-30°C

SMILES字符串

[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

一般描述

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.

应用

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.

象形图

CorrosionExclamation mark
GHS05,GHS07

警示用语：

Danger

危险分类

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

靶器官

Respiratory system

储存分类代码

8A - Combustible, corrosive hazardous materials

WGK

WGK 1

闪点(°F)

332.1 °F - Pensky-Martens closed cup

闪点(°C)

> 166.7 °C - Pensky-Martens closed cup

分析证书(COA)

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Highly efficient p-toluenesulfonic acid-catalyzed alcohol addition or hydration of unsymmetrical arylalkynes
Olivi N, et al.
Synlett, 2004, 2175-2179 (2004)
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)
L. R. Subramanian, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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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