Bis(2-methoxyethyl)aminosulfur trifluoride

Description

Deoxo-Fluor is a nucleophilic fluorinating agent with wide use in organic chemistry. Deoxo-Fluor is more thermally stable than Diethylaminosulfur Trifluoride (DAST).

Chemical properties

Dark yellow-orange liquid

The Uses of Bis(2-methoxyethyl)aminosulfur trifluoride

Versatile, thermally stable nucleophilic fluorinating reagent.

The Uses of Bis(2-methoxyethyl)aminosulfur trifluoride

The SM (50 mg, 0.135 mmol) was dissolved in anhydrous DCM (2 mL), and the mixture was cooled to 0 C. Deoxo-Fluor (0.074 mL, 0.404 mmol) was added dropwise, the reaction mixture was stirred at 0 C for 1 h, and then allowed to reach RT over 14 h. The mixture was quenched with MeOH (1 mL) and the solvent was removed in vacuo. The residue was purified by flash chromatography to provide the product as a white solid. [50 mg, 99%]

The Uses of Bis(2-methoxyethyl)aminosulfur trifluoride

Reactant for:

• Fluorination reactions
• Preparation of fluorinated catechols via Umpolung based nucleophilic deoxyfluorination
• Preparation of imidazole derivatives as CXCR3 antagonists
• Ring expansion reactions
• Synthesis of acyl azides from carboxylic acids
• Aldehydes or ketones from carboxylic acids and Grignard reagents via in situ generation of Weinreb amides