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Diethylaminosulfur trifluoride (DAST) is used as a precursor to prepare 2,6-dimethoxybenzoyl fluoride and 2-thiazolines. It is a useful fluorinating agent used for a variety of compounds including alcohols, thioethers, alkenols and cyanohydrins. It also serves as a catalyst for Friedel-Crafts allylation reaction using tertiary cyclopropyl silyl ethers and in the rearrangement of homoallylic alcohols to unsaturated aldehydes. It plays an important role for gem difluorination of ketopipecolinic acids.
Reagent for conversion of alcohols to alkyl fluorides and carbonyl compounds to gem-difluorides, less prone to cause dehydration or rearrangement than SF4: J. Org. Chem., 40, 574 (1975); Org. Synth. Coll., 6, 835 (1988); Eur. J. Org. Chem., 3177 (2000); Tetrahedron Lett, 44, 6661 (2003); reviews: Org. React., 35, 513 (1988); Austral. J. Chem., 54, 75 (2001); Synlett, 1130 (2006). Conversion of alcohols to fluorides has been accomplished with stereocontrol at the chiral center: Tetrahedron: Asym., 4, 161 (1993).
Use of dichloromethane as solvent permits the selective monofluorination of sugars: J. Org. Chem., 48, 393 (1983). Glycosyl fluorides, which are useful building blocks for oligosaccharides: J. Am. Chem. Soc., 105, 2430 (1983), and C-glycosides, can be prepared by reaction of DAST with phenylthioglycosides: J. Am. Chem. Soc., 106, 4189 (1984). The reaction with diols can lead to difluorides, sulfite esters or cyclic ethers: J. Chem. Soc., Perkin 2, 861 (1995).
Convenient reagent for conversion, in the absence of base, of N-protected amino acids to the acyl fluorides: Lett. Pept. Sci., 2, 285 (1996); Indian J. Chem., 39, 384 (2000); compare Cyanuric fluoride, A15666. Review of peptide coupling via amino acid halides: Acc. Chem. Res., 29, 268 (1996). See also Appendix 6.
In the presence of SbCl3, promotes the fluoro-Pummerer rearrangement of sulfoxides: J. Am. Chem. Soc., 107, 735 (1985); Org. Synth. Coll., 9, 446 (1998):
Direct conversion of thioethers to the ɑ-fluoro analogues has also been reported: J. Org. Chem., 58, 3800 (1993). Fluorination of thioesters leads to ɑɑ-difluoroethers: J. Org. Chem., 55, 768 (1990):
See also 4-Morpholinylsulfur trifluoride, L19751.
Gao, X.; Tang, X. Effective reduction of graphene oxide thin films by a fluorinating agent: Diethylaminosulfur trifluoride. Carbon 2014, 76, 133-140.
Anxionnat, B.; Robert, B.; George, P.; Ricci, G.; Perrin, M. A.; Pardo, D. G.; Cossy, J. Correction to Ring Expansion of Cyclic beta-Amino Alcohols Induced by Diethylaminosulfur Trifluoride: Synthesis of Cyclic Amines with a Tertiary Fluoride at C3. J. Org. Chem. 2014, 77 (14), 6087-6099.
Hazard Statements: H226-H302-H312-H314-H332-H335
Flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant