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Safety Information

719439

Sigma-Aldrich

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
MDL number:
MFCD15144877
UNSPSC Code:
12352101
PubChem Substance ID:
329763649
NACRES:
NA.22

form

solid

Quality Level

100

mp

84-87 °C

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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

JAN Code

719439-VAR:
719439-25G:4548173301075
719439-50G:
719439-1KG:
719439-5G:4548173301082
719439-250G:4548173304878
719439-BULK:
719439-100G:

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Certificates of Analysis (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

Articles

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

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

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