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MilliporeSigma

158534

Trifluoromethanesulfonic acid

reagent grade, 98%, liquid

Synonym(s):

TFMSA, Triflic acid

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$47.40

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$122.00

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$193.00

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About This Item

Linear Formula:
CF3SO3H
CAS Number:
Molecular Weight:
150.08
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
216-087-5
MDL number:
Beilstein/REAXYS Number:
1812100
Assay:
98%
Form:
liquid
Grade:
reagent grade

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Product Name

Trifluoromethanesulfonic acid, reagent grade, 98%

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)

assay

98%

form

liquid

refractive index

n20/D 1.327 (lit.)

Quality Level

pH

0.11

bp

162 °C (lit.)

solubility

water: soluble 1.600 g/L at 20 °C

density

1.696 g/mL at 25 °C (lit.)

functional group

fluoro
triflate

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1 of 4

This Item
3478178.211661.08450
grade

reagent grade

grade

reagent grade

grade

-

grade

-

assay

98%

assay

≥99%

assay

-

assay

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.327 (lit.)

refractive index

n20/D 1.327 (lit.)

refractive index

-

refractive index

-

vapor density

5.2 (vs air)

vapor density

5.2 (vs air)

vapor density

-

vapor density

-

Application

Deglycosylation agent
Trifluoromethanesulfonic acid is a versatile reagent[1], employed as catalyst for the following studies:
  • Friedel-Crafts acylation of aromatic compounds with methyl benzoate.[2]
  • Addition reaction of dialkyl disulfides to terminal alkynes.[3]
  • Synthesis of a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS).[4]
  • Preparation of starting reagents for the synthesis of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives.[5]
  • Synthesis of aryl triflates,[6] the lactonization of alkenoic acids,[7] and the formation of E-alkenes.[8]
Trifluoromethanesulfonic acid may be used as an initiator for the cationic polymerization of styrene[9], hexamethylcyclotrisiloxane[10] and L,L-dilactide.[11]

General description

Trifluoromethanesulfonic acid is the strongest monoprotic organic acid. It has been synthesized by the oxidation of bis(trifluoromethylthio)mercury with aqueous hydrogen peroxide.[12] It undergoes complete dissociation in basic solvents such as dimethyl sulfoxide, dimethylacetamide and dimethylformamide. Its dissociation in non-aqueous solvents has been studied by conductometry.[12] On mixing trifluoromethanesulfonic acid with HNO3, it forms nitronium trifluoromethane sulfonate, which is an excellent nitrating reagent.[13]

pictograms

CorrosionExclamation mark

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


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Cationic polymerization of hexamethylcyclotrisiloxane by trifluoromethanesulfonic acid and its derivatives, 2. Reaction involving activated trifluoromethylsulfonates.
Toskas G, et al.
Macromolecular Chemistry and Physics, 196(9), 2715-2735 (1995)
Shota Kinoshita et al.
Journal of the American Chemical Society, 137(15), 5061-5065 (2015-04-01)
In this study, a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS) was selectively prepared by the hydrolytic condensation of 3-aminopropyldiethoxymethylsilane using aqueous superacid trifluoromethanesulfonic acid. The (1)H NMR spectrum of Am-CyTS in D2O exhibited a single
Tetrahedron, 49, 7119-7119 (1993)
Determination of the rate constants of the elementary steps in the cationic polymerization of styrene by trifluoromethanesulfonic acid.
Kunitake T and Takarabe K.
Macromolecules, 12(6), 1061-1067 (1979)
Meilin Li et al.
Archiv der Pharmazie, 348(5), 353-365 (2015-04-01)
A new series of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives were synthesized from starting compounds 3a-i, which were prepared from acrylic acid ethyl ester and the appropriate amines using trifluoromethanesulfonic acid as a catalyst. A total of 9 novel derivatives were synthesized

Articles

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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