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906190

Sigma-Aldrich

1,2-Dibromoethane-1-sulfonyl fluoride

Synonym(e):

DESF, SuFEx hub, SuFEx-able plugin

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About This Item

Empirische Formel (Hill-System):
C2H3Br2FO2S
CAS-Nummer:
103020-97-9
Molekulargewicht:
269.92
MDL-Nummer:
MFCD31615713
UNSPSC-Code:
12352101
NACRES:
NA.22

Form

liquid

Eignung der Reaktion

reaction type: click chemistry

SMILES String

F[S](=O)(=O)C(Br)CBr

InChIKey

NIJDNCLEFCJVRL-UHFFFAOYSA-N

Verwandte Kategorien

Anwendung

1,2-Dibromoethane-1-sulfonyl fluoride (DESF) is a bench-stable precursor to 1-bromoethene-1-sulfonyl fluoride (BESF), a new and robust connective hub for the Sulfur (VI) fluoride exchange (SuFEx) click reaction. BESF offers similar routes as ethenesulfonyl fluoride (ESF, cat# 746959) but with additional reactivity due to the embedded bromo group.

Treatment of DESF with triethylamine generates BESF in situ, which has been used to synthesize diverse and unprecented sulfonyl fluorides in good-to-excellent yields. As the resulting molecules possess sulfonyl fluoride handles, further SuFEx reactions are also possible. DESF adds another useful tool for conjugation strategies in chemical biology and organic and polymer synthesis.

Automate your fluorination reactions with Synple Automated Synthesis Platform (SYNPLE-SC002)

Sonstige Hinweise

1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry

Regioselective Synthesis of Fluorosulfonyl 1,2,3-Triazoles from Bromovinylsulfonyl Fluoride

Technology Spotlight: SuFEx: Sulfonyl Fluorides that Participate in the Next Click Reaction

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Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H315,H319

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Analysenzertifikate (COA)

Lot/Batch Number

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Jing Leng et al.
Chemical communications (Cambridge, England), 54(35), 4477-4480 (2018-04-17)
A new fluorosulfonylation reagent 1-bromoethene-1-sulfonyl fluoride was developed (1-Br-ESF). This unique reagent possesses three addressable handles (vinyl, bromide, and sulfonyl fluoride) and has great potential to function as a tris-electrophile and as a sulfur(vi) fluoride exchange (SuFEx) clickable material to
Joice Thomas et al.
Organic letters, 20(13), 3749-3752 (2018-06-16)
A regioselective metal-free preparation of 4-fluorosulfonyl 1,2,3-triazoles from organic azides and a hitherto underexplored bromovinylsulfonyl fluoride building block is described. This reaction is very general and was extended to the synthesis of various sulfonates, sulfonamides, and sulfonic acid derivatives of
Christopher J Smedley et al.
Chemical communications (Cambridge, England), 54(47), 6020-6023 (2018-05-26)
We demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride (BESF). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the syntheses of

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