347817
Trifluoromethanesulfonic acid
ReagentPlus®, ≥99%
Synonym(s):
Triflic acid
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About This Item
Linear Formula:
CF3SO3H
CAS Number:
Molecular Weight:
150.08
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
EC Number:
216-087-5
Beilstein/REAXYS Number:
1812100
MDL number:
Assay:
≥99%
Form:
liquid
Grade:
reagent grade
grade
reagent grade
Quality Level
vapor density
5.2 (vs air)
vapor pressure
8 mmHg ( 25 °C)
product line
ReagentPlus®
assay
≥99%
form
liquid
refractive index
n20/D 1.327 (lit.)
bp
162 °C (lit.)
mp
- 40 °C
solubility
1,600 g/L at 20 °C
density
1.696 g/mL at 25 °C (lit.)
functional group
fluoro, triflate
SMILES string
OS(=O)(=O)C(F)(F)F
InChI
1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
InChI key
ITMCEJHCFYSIIV-UHFFFAOYSA-N
General description
Trifluoromethanesulfonic acid is a strong organic acid. It can be prepared by reacting bis(trifluoromethylthio)mercury with H2O2. On mixing with HNO3, it affords a nitrating reagent (a nitronium salt). This reagent is useful for the nitration of aromatic compounds. Its dissociation in various organic solvents has been studied.
Application
Trifluoromethanesulfonic acid can be used as a catalyst to prepare:
It can also be used as a catalyst in the Fischer glycosylation and Friedel-Crafts acylation reactions.
- Substituted tetrahydrofurans and tetrahydropyrans by cyclization of corresponding unsaturated alcohols under acidic conditions.
- Nitriles from corresponding aldehydes by Schmidt reaction.
- Disubstituted five-membered ring lactones by allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes.
It can also be used as a catalyst in the Fischer glycosylation and Friedel-Crafts acylation reactions.
Deglycosylation agent
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3
target_organs
Respiratory system
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 1
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Use of trifluoromethanesulfonic acid in fischer glycosylations.
Wessel HP.
Journal of Carbohydrate Chemistry, 7(1), 263-269 (1988)
Aromatic nitration with nitric acid and trifluoromethanesulfonic acid.
Coon CL, et al.
The Journal of Organic Chemistry, 38(25), 4243-4248 (1973)
Trifluoromethanesulfonic acid and derivatives.
Howells RD and Cown JDM.
Chemical Reviews, 77(1), 69-92 (1977)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 347817-100G | 04061833313824 |
| 347817-25G | 04061826761816 |
| 347817-500G | 04061826761830 |
| 347817-5G | 04061826761854 |
| 347817-5X1G | 04061838102973 |