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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
Pricing and availability is not currently available.

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.)

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

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Application

Perfluoro-1-butanesulfonyl fluoride (NfF) reacts with alcohols, including phenols, to yield nonafluorobutanesulfonate esters (nonaflates).[1][2] Nonaflates can be used as electrophiles in several palladium-catalyzed cross coupling reactions[3][4] and in Buchwald-Hartwig amination.[5]
NfF can also be used to prepare aryl nonaflates by reacting with corresponding aryloxysilanes in the presence of fluoride ion.[6]

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Product No.
Description
Pricing

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB2295
STBL0285
STBK1166
STBJ5100
STBG4727V

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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)
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)
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Questions

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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      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/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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