906190
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:
Molekulargewicht:
269.92
MDL-Nummer:
UNSPSC-Code:
12352101
NACRES:
NA.22
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Form
liquid
Eignung der Reaktion
reaction type: click chemistry
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.
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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)
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Signalwort
Warning
H-Sätze
Gefahreneinstufungen
Eye Irrit. 2 - Skin Irrit. 2
Lagerklassenschlüssel
10 - Combustible liquids
WGK
WGK 3
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
Analysenzertifikate (COA)
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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
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
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
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