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77283

Sigma-Aldrich

Heptadecafluorooctanesulfonic acid solution

~40% in H2O (T)

Synonym(s):

PFOS, Perfluorooctanesulfonic acid

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About This Item

Linear Formula:
CF3(CF2)7SO3H
CAS Number:
1763-23-1
Molecular Weight:
500.13
Beilstein:
1813859
MDL number:
MFCD00042454
UNSPSC Code:
12352100
PubChem Substance ID:
57652692
NACRES:
NA.22

form

liquid

concentration

~40% in H2O (T)

functional group

fluoro
sulfonic acid

SMILES string

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

InChI

1S/C8HF17O3S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28/h(H,26,27,28)

InChI key

YFSUTJLHUFNCNZ-UHFFFAOYSA-N

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Application

Heptadecafluorooctanesulfonic acid solution can be used as a catalyst:
  • In the benzoylation of a variety of unactivated benzenes via Friedel-Crafts acylation reaction in the presence of rare earth(III) perfluorooctane sulfonate in fluorous solvents.
  • For the dinitration of aromatic compounds to synthesize dinitrobenzenes in the presence of ytterbium perfluorooctane sulfonate and fluorous solvent.
  • To synthesize tetrahydroisoquinoline derivatives via Pictet-Spengler reaction of β-arylethyl carbamates with aldehydes.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2 - Lact. - Repr. 1B - STOT RE 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBB9965
1420625V
1420625
1269901
014357/1

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Rare earth (III) perfluorooctane sulfonates and perfluorooctanesulfonic acid in fluorous solvents: Novel and recyclable catalytic systems for Friedel-Crafts acylation of unactivated benzenes
Yi W, et al.
Journal of Fluorine Chemistry, 126, 1191-1195 (2005)
Highly efficient dinitration of aromatic compounds in fluorous media using ytterbium perfluorooctanesulfonate and perfluorooctanesulfonic acid as catalysts
Yi W, et al.
Synthetic Communications, 36, 2957-2961 (2006)
Pictet-Spengler reactions catalyzed by Bronsted acid-surfactant-combined catalyst in water or aqueous media
Saito A, et al.
Tetrahedron Letters, 48, 835-839 (2007)
Michio Murakami et al.
Chemosphere, 93(1), 140-145 (2013-06-12)
The formation of perfluorinated surfactants (PFSs) from their precursors in waters is of concern. In this study, the formation of PFSs through biodegradation of precursors was measured in incubation tests. Indigenous microorganisms in groundwater were able to biodegrade perfluorooctane sulfonamide
Shahid Ullah et al.
Environment international, 65, 63-72 (2014-01-29)
A method was developed for simultaneous analysis of perfluoroalkane sulfonic acids (PFSAs) and their sulfonamide-based precursors (perfluoroalkane sulfonamidoacetic acids (FASAAs), sulfonamides (FASAs), and sulfonamidoethanols (FASEs)) in fish muscle. Extraction was performed with acetonitrile followed by a clean-up and fractionation step
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