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319732

Sigma-Aldrich

Perfluoro-1-butanesulfonyl fluoride

96%

Synonym(s):

NfF, Nonafluorobutanesulfonyl fluoride

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About This Item

Linear Formula:
CF3(CF2)3SO2F
CAS Number:
375-72-4
Molecular Weight:
302.09
EC Number:
206-792-6
MDL number:
MFCD00007422
UNSPSC Code:
12352100
PubChem Substance ID:
24859184
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.3 (lit.)

bp

64 °C (lit.)

density

1.682 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O

InChI

1S/C4F10O2S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16

InChI key

LUYQYZLEHLTPBH-UHFFFAOYSA-N

Application

Perfluoro-1-butanesulfonyl fluoride (NfF) reacts with alcohols, including phenols, to yield nonafluorobutanesulfonate esters (nonaflates). Nonaflates can be used as electrophiles in several palladium-catalyzed cross coupling reactions and in Buchwald-Hartwig amination.
NfF can also be used to prepare aryl nonaflates by reacting with corresponding aryloxysilanes in the presence of fluoride ion.

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Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium-catalyzed amination of aryl nonaflates.
Anderson KW, et al.
The Journal of Organic Chemistry, 68(25), 9563-9573 (2003)
Synthesis of polysubstituted olefins by Pd-catalyzed cross-coupling reaction of tosylhydrazones and aryl nonaflates.
Barluenga J, et al.
Organic Letters, 13(3), 510-513 (2010)
Hydrierende Spaltung phenolischer und enolischer Perfluoroalkansulfonate.
Subramanian L R, et al.
Synthesis, 1984(06), 481-485 (1984)
A general method for palladium-catalyzed reactions of primary sulfonamides with aryl nonaflates.
Shekhar S, et al.
The Journal of Organic Chemistry, 76(11), 4552-4563 (2011)
Facile synthesis of trifluoro-and hexafluoroisopropyl halides.
Hanack M and Ullmann J
The Journal of Organic Chemistry, 54(6), 1432-1435 (1989)
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