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Merck

347817

Trifluoromethanesulfonic acid

ReagentPlus®, ≥99%

Synonym(s):

Triflic acid

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About This Item

Linear Formula:
CF3SO3H
CAS Number:
1493-13-6
Molecular Weight:
150.08
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
24861529
EC Number:
216-087-5
Beilstein/REAXYS Number:
1812100
MDL number:
MFCD00007514
Assay:
≥99%
Form:
liquid
Grade:
reagent grade

Key Documents

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InChI key

ITMCEJHCFYSIIV-UHFFFAOYSA-N

InChI

1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)

SMILES string

OS(=O)(=O)C(F)(F)F

grade

reagent grade

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

Quality Level

200

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Application

Deglycosylation agent
Trifluoromethanesulfonic acid can be used as a catalyst to prepare:
  • 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.

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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

347817-1G-KC: + 347817-100G:4548173310572 + 347817-5X1G:4548173138671 + 347817-1G:4548173138640 + 347817-5G:4548173138664 + 347817-BULK: + 347817-VAR: + 347817-500G:4548173321042 + 347817-5X1G-KC: + 347817-25G:4548173138657

jan

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9347
MKCM5936
MKCM2349
MKCL2453
MKCH5602

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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)
Electrochemical studies of sulfonates in non-aqueous solvents: Part III. Trifluoromethanesulfonic acid as a strong acid in dipolar aprotic solvents and acetic acid.
Fujinaga T and Sakamoto I.
J. Electroanal. Chem. Interfac. Electrochem., 85(1), 185-201 (1977)
Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry
Elford TG, et al.
The Journal of Organic Chemistry, 72(4), 1276-1284 (2007)
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