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Sigma-Aldrich

XtalFluor-E®

Synonym(e):

DAST-difluorsulfinium-Salz, (Diethylamino)-difluorsulfonium-tetrafluoroborat, N,N-Diethyl-S,S-difluorsulfiliminiumtetrafluoroborat, N,N-Diethylamino-S,S-difluorsulfiniumtetrafluoroborat, N-(Difluor-λ4-sulfanyliden)-N-ethyl-ethanaminium-tetrafluoroborat

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About This Item

Empirische Formel (Hill-System):
C4H10BF6NS
CAS-Nummer:
63517-29-3
Molekulargewicht:
229.00
MDL-Nummer:
MFCD15144877
UNSPSC-Code:
12352101
PubChem Substanz-ID:
329763649
NACRES:
NA.22

Form

solid

mp (Schmelzpunkt)

84-87 °C

Lagertemp.

−20°C

SMILES String

F[B-](F)(F)F.CC\[N+](CC)=S(\F)F

InChI

1S/C4H10F2NS.BF4/c1-3-7(4-2)8(5)6;2-1(3,4)5/h3-4H2,1-2H3;/q+1;-1

InChIKey

YLNKFQWRRIXZPJ-UHFFFAOYSA-N

Allgemeine Beschreibung

XtalFluor-E® is widely used in formylation, ring expansion, proto-functionalization, cyclodehydration, and dehydration.

Anwendung

Convenient crystalline highly chemoselective deoxofluorination reagent with a broad substrate scope

Deoxofluorination reagent with a better safety profile, that doesn′t generate corrosive HF which makes it suitable for use in standard borosilicate vessels, and does not react violently with water

Reactant for:
  • Preparation of fluorodisaccharides
Triisopropylsilanethiol was recently reported by MacMillian and coworkers to be used as an organocatalyst, in tandem with Ir(III) specifically Aldrich product 688096, in photoredox catalysis. This approach directly couples a cyano-containing arene with an allylic sp3 C-H bond.

Sonstige Hinweise

The direct arylation of allylic sp3 C–H bonds via organic and photoredox catalysis

Rechtliche Hinweise

XtalFluor-E is a registered trademark of OmegaChem, Inc.

Piktogramme

Skull and crossbonesCorrosion
GHS06,GHS05

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B

Zusätzliche Gefahrenhinweise

EUH014

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

Melinda Nonn et al.
Organic letters, 17(5), 1074-1077 (2015-02-17)
The selective introduction of fluorine onto the skeleton of an aminocyclopentane or cyclohexane carboxylate has been developed through a novel and efficient fluoride opening of an activated aziridine ring with XtalFluor-E. The reaction proceeded through a stereoselective aziridination of the
Francis Beaulieu et al.
Organic letters, 11(21), 5050-5053 (2009-10-06)
Aminodifluorosulfinium tetrafluoroborate salts were found to act as efficient deoxofluorinating reagents when promoted by an exogenous fluoride source and, in most cases, exhibited greater selectivity by providing less elimination byproduct as compared to DAST and Deoxo-Fluor. Aminodifluorosulfinium tetrafluoroborates are easy
Alexandre L'heureux et al.
The Journal of organic chemistry, 75(10), 3401-3411 (2010-04-22)
Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding

Artikel

XtalFluor-E® and XtalFluor-M®: Convenient, Crystalline Deoxofluorination Reagents

Sigma-Aldrich.com presents an article regarding XtalFluor-E® and XtalFluor-M®: Convenient, Crystalline Deoxofluorination Reagents.

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