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392715

Sigma-Aldrich

N-Fluorobenzenesulfonimide

97%

Synonym(s):

N-Fluorodi(benzenesulfonyl)amine, N-Fluorodibenzenesulfonimide, NFSI

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About This Item

Linear Formula:
(C6H5SO2)2NF
CAS Number:
133745-75-2
Molecular Weight:
315.34
Beilstein:
5348902
MDL number:
MFCD00144885
UNSPSC Code:
12352101
PubChem Substance ID:
24864479
NACRES:
NA.22
form:
powder
Assay:
97%

₪447.00

Please contact Customer Service for Availability
Request a Bulk Order

Quality Level

100

Assay

97%

form

powder

mp

110 °C (dec.) (lit.)

SMILES string

FN(S(=O)(=O)c1ccccc1)S(=O)(=O)c2ccccc2

InChI

1S/C12H10FNO4S2/c13-14(19(15,16)11-7-3-1-4-8-11)20(17,18)12-9-5-2-6-10-12/h1-10H

InChI key

RLKHFSNWQCZBDC-UHFFFAOYSA-N

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General description

N-Fluorobenzenesulfonimide (NFSi) is a commonly used electrophilic fluorinating agent in organic synthesis to introduce fluorine into neutral organic molecules. It is also used to fluorinate nucleophilic substrates such as reactive organometallic species and malonate anions.[1][2]
NFSi can be synthesized by the reaction of benzenesulfonimide with fluorine.[1]

Application

Reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams.[3] Also used in the electrophilic difluorination of dihalopyridines with butyl lithium[4] and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.[5]
Stable, easy-to-handle, crystalline material which readily transfers F+ to enolates and carbanions.[6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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
MKCT6701
MKCP6556
MKBT6296V
MKBD7674V
MKBJ4142V

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Toshiaki Suzuki et al.
The Journal of organic chemistry, 72(1), 246-250 (2006-12-30)
An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates
N-fluorobenzenesulfonimide
Bizet V
Synlett, 23(18), 2719-2720 (2012)
Tetrahedron Letters, 47, 8457-8457 (2006)
N-Fluorobenzenesulfonimide
Poss AJ
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 23(18), 2719-2720 (2001)
Anthony A Fodor et al.
The Journal of general physiology, 127(6), 755-766 (2006-06-01)
The study of ion channel function is constrained by the availability of structures for only a small number of channels. A commonly used bioinformatics technique is to assert, based on sequence similarity, that a domain within a channel of interest
View All Related Papers

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

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    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    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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