38078-09-0 | Diethylaminosulfur trifluoride

CAS:38078-09-0 | Diethylaminosulfur trifluoride ,Description

Diethylaminosulfur trifluoride (DESF) is an organosulfur compound with the chemical formula C2H5NSF3. It is a colorless, non-flammable liquid with a melting point of -45.8°C. DESF was first synthesized in the late 1950s and has since been used for a variety of applications in the fields of chemistry, biochemistry, and medicine. 
 

Scientific Research Applications

• Monofluorination of Trifluoromethyl Substituted Chromenones:
  • DAST has been effectively used in monofluorination reactions of trifluoromethyl substituted chromenones. This process employs a mild and efficient methodology to synthesize fluorinated compounds (2-fluoro-chromenones) through a chemoselective reaction with yields ranging from 63% to 81% (Bonacorso et al., 2011).
• Thermal Stability and Hazard Potential:
  • DAST can decompose violently when heated, presenting a hazard if not handled properly. Its decomposition occurs in two steps, initially forming sulfur tetrafluoride and bis(diethylamino) sulfur difluoride, followed by a vigorous exothermic decomposition of the less stable difluoride (Messina et al., 1989).
• Synthesis of Fluorinated Nucleosides:
  • DAST has been applied as a fluorinating agent in the synthesis of nucleosides fluorinated in the carbohydrate moiety. This showcases its utility in modifying nucleosides, which are fundamental to genetic material (Herdewijn et al., 1989).
• Fluorination of N-Aryl-N-Hydroxyamides:
  • DAST has been used to fluorinate N-aryl-N-hydroxyamides, replacing the hydroxy function with a fluorine atom at the para position of the aromatic ring, resulting in high yields (Kikugawa et al., 1992).
• Perfluoroalkylthiolation Reactions:
  • Trifluoromethyl diethylaminosulfur difluoride (CF3-DAST), an analogue of DAST, is efficient for trifluoromethylthiolation of α-methylene-β-keto esters and sulfones, demonstrating DAST's versatility in organic synthesis (Saidalimu et al., 2016).
• Double Thiolation Reagent for Imidazo[1,2-α]pyridines:
  • DAST has been reported as a novel, cost-effective double thiolation reagent for sulfurizing a range of imidazo[1,2-α]pyridines under mild conditions, expanding its applications beyond fluorination (Jiang et al., 2021).
• Fluorinative Beckmann Fragmentation:
  • DAST facilitates fluorinative fragmentation of cyclic ketoximes, offering a pathway to produce fluorinated carbonitrile. This method highlights DAST's role in introducing fluorine into organic compounds (Kirihara et al., 2000).
• Dehydration, Cyclization, and Fluorination of Pyrazoles:
  • DAST is used in the dehydration, intramolecular cyclization, and fluorination of pyrazoles and pyrazolines, demonstrating its multifaceted role in organic synthesis (Bonacorso et al., 2010).
• Efficient Synthesis of Fluorinated Benzamide Neuroleptic:
  • DAST played a crucial role in the synthesis of fluorinated benzamides, showcasing its importance in pharmaceutical chemistry (Mukherjee, 1990).
• Recyclable Solvents for Fluorination:
  • Research has shown the use of ionic liquids as recyclable solvents for DAST-mediated fluorination of alcohols and carbonyl compounds, highlighting DAST's compatibility with green chemistry principles (Das et al., 2007).

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