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719439

Sigma-Aldrich

XtalFluor-E®

Synonyme(s) :

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

Formule empirique (notation de Hill):
C4H10BF6NS
Numéro CAS:
63517-29-3
Poids moléculaire :
229.00
Numéro MDL:
MFCD15144877
Code UNSPSC :
12352101
ID de substance PubChem :
329763649
Nomenclature NACRES :
NA.22

Forme

solid

Niveau de qualité

100

Pf

84-87 °C

Groupe fonctionnel

amine

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

YLNKFQWRRIXZPJ-UHFFFAOYSA-N

Description générale

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

Application

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.

Autres remarques

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

Informations légales

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

Pictogrammes

Skull and crossbonesCorrosion
GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H301 + H311 + H331,H314

Classification des risques

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

Risques supp

EUH014

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
MKCT8138
MKCV1874
MKCP4977
MKCN4471
MKCN1078

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
XtalFluor-E: A useful and versatile reagent in organic transformations
Mohammadkhani L and Heravi MM
Journal of Fluorine Chemistry, 225, 11-20 (2019)
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

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