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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Related Experiment Video

Updated: May 14, 2026

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)
08:33

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)

Published on: June 28, 2011

Next-Gen 18F-Relay Reagent: Optimising [18F]Ethanesulfonyl Fluoride.

Margaret L Aulsebrook1, Giancarlo Pascali2, Kellie L Tuck3

  • 1Monash Biomedical Imaging, Monash University, Melbourne, VIC 3800, Australia.

International Journal of Molecular Sciences
|May 13, 2026
PubMed
Summary
This summary is machine-generated.

A new radiolabeling reagent, [18F]ethanesulfonyl fluoride ([18F]E-SF), offers an efficient alternative to conventional methods. It bypasses drying steps and shows high yields in producing [18F]labeled compounds.

Keywords:
fluorinepositron emission tomographyradiofluorinationradiopharmaceuticalssulfonyl fluoride

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Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)
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Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
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Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling

Published on: November 11, 2008

Area of Science:

  • Radiochemistry
  • Nuclear Medicine
  • Organic Synthesis

Background:

  • Conventional nucleophilic radiofluorination using [18F]fluoride necessitates azeotropic drying, leading to delays and activity loss.
  • [18F]Fluoride relay reagents like [18F]triflyl fluoride ([18F]TfF) and [18F]ethenesulfonyl fluoride ([18F]E=SF) offer improved efficiency by circumventing this drying step.

Purpose of the Study:

  • To introduce and evaluate [18F]ethanesulfonyl fluoride ([18F]E-SF) as a novel [18F]fluoride relay reagent.
  • To benchmark the production and radiolabeling performance of [18F]E-SF against existing reagents ([18F]TfF and [18F]E=SF).

Main Methods:

  • [18F]E-SF was synthesized from commercially available 2,4,6-trichlorophenyl-1-ethanesulfonate (TCP-ethane) via microlitre-scale radiofluorination.
  • Optimized conditions were used for direct distillation and solid-phase extraction (SPE) trapping of [18F]E-SF.
  • Model labeling reactions were performed to assess the utility of [18F]E-SF in aliphatic and aromatic nucleophilic substitutions.

Main Results:

  • [18F]E-SF was obtained in high radiochemical yields (RCY) of 76 ± 23% (n=6).
  • Performance was compared to [18F]E=SF (27 ± 6%, n=2) and [18F]TfF (up to 97 ± 2%, n=3).
  • Subsequent labeling reactions demonstrated efficient conversion to [18F]fluoroethyl tosylate and [18F]fluorobenzaldehyde.

Conclusions:

  • [18F]E-SF is a robust and user-friendly relay reagent with high production yields from a readily available precursor.
  • Its compatibility with SPE trapping and comparable yields to [18F]TfF and [18F]E=SF support its potential for automated production.
  • This reagent facilitates streamlined and decentralized 18F-labeling workflows.