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719439

XtalFluor-E®

Synonym(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

Empirical Formula (Hill Notation):
C4H10BF6NS
CAS Number:
63517-29-3
Molecular Weight:
229.00
NACRES:
NA.22
PubChem Substance ID:
329763649
UNSPSC Code:
12352101
MDL number:
MFCD15144877
Form:
solid
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form

solid

Quality Level

100

mp

84-87 °C

functional group

amine

storage temp.

−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

InChI key

YLNKFQWRRIXZPJ-UHFFFAOYSA-N

General description

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.

Other Notes

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

Legal Information

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

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4089
MKCZ4088
MKCT8138
MKCV1874
MKCP4977

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Articles

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

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

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

Global Trade Item Number

SKUGTIN
719439-1KG04061826680735
719439-5G04061832855295
719439-250G04061833565131
719439-25G04061833358849