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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:
Molecular Weight:
302.09
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

functional group

fluoro

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

Signal Word

Danger

Hazard Statements

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

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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)
Uber Perfluoralkansulfonsaurearylester.
Niederprum H, et al.
European Journal of Organic Chemistry, 1973(1), 20-32 (1973)
Facile synthesis of trifluoro-and hexafluoroisopropyl halides.
Hanack M and Ullmann J
The Journal of Organic Chemistry, 54(6), 1432-1435 (1989)
Palladium-catalyzed amination of aryl nonaflates.
Anderson KW, et al.
The Journal of Organic Chemistry, 68(25), 9563-9573 (2003)
Hydrierende Spaltung phenolischer und enolischer Perfluoroalkansulfonate.
Subramanian L R, et al.
Synthesis, 1984(06), 481-485 (1984)

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