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719439

Sigma-Aldrich

XtalFluor-E®

Sinonimo/i:

DAST difluorosulfinium salt, (Diethylamino)difluorosulfonium tetrafluoroborate, N,N-Diethyl-S,S-difluorosulfiliminium tetrafluoroborate, N,N-Diethylamino-S,S-difluorosulfinium tetrafluoroborate, N-(Difluoro-λ4-sulfanylidene)-N-ethyl-ethanaminium tetrafluoroborate

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About This Item

Formula empirica (notazione di Hill):
C4H10BF6NS
Numero CAS:
63517-29-3
Peso molecolare:
229.00
Numero MDL:
MFCD15144877
Codice UNSPSC:
12352101
ID PubChem:
329763649
NACRES:
NA.22

Stato

solid

Livello qualitativo

100

Punto di fusione

84-87 °C

Gruppo funzionale

amine

Temperatura di conservazione

−20°C

Stringa SMILE

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
YLNKFQWRRIXZPJ-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

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

Applicazioni

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.

Altre note

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

Note legali

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

Pittogrammi

Skull and crossbonesCorrosion
GHS06,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H301 + H311 + H331,H314

Classi di pericolo

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

Rischi supp

EUH014

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
MKCP4977
MKCN4471
MKCN1078
MKCN1080
MKCM8660

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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

Articoli

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

This is an article regarding XtalFluor-E® and XtalFluor-M®: Convenient, Crystalline Deoxofluorination Reagents.

Global Trade Item Number

SKUGTIN
719439-1KG4061826680735
719439-50G
719439-5G4061832855295
719439-100G
719439-250G4061833565131
719439-25G4061833358849

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