All Photos(1)

319732

Sigma-Aldrich

Perfluoro-1-butanesulfonyl fluoride

96%

Synonym(s):
NfF, Nonafluorobutanesulfonyl fluoride
Linear Formula:
CF3(CF2)3SO2F
CAS Number:
Molecular Weight:
302.09
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

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.

Packaging

25, 100 g in poly bottle

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8B - Non-combustible, corrosive hazardous materials

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Hydrierende Spaltung phenolischer und enolischer Perfluoroalkansulfonate.
Subramanian L R, et al.
Synthesis, 1984(06), 481-485 (1984)
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)
Uber Perfluoralkansulfonsaurearylester.
Niederprum H, et al.
European Journal of Organic Chemistry, 1973(1), 20-32 (1973)
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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