Diethylaminosulfur trifluoride

• Catalog No.: A11992
• CAS Number: 38078-09-0
• M. F.: C4H10F3NS
• M. W.: 161.1891096
• Purity: 95%

SYNONYMS

• Title: 二乙氨基三氟化硫
• IUPAC name: diethyl(trifluoro-λ^4-sulfanyl)amine
• IUPAC Traditional name: diethylaminosulfur trifluoride
• Synonyms: DAST

DATABASE IDS

• MDL Number: MFCD00000363
• Beilstein Number: 1849066
• CAS Number: 38078-09-0
• EC Number: 253-771-2

PROPERTIES

• Purity: 95%
• Boiling Point: 30-32°C/3mm
• Density: 1.23
• Flash Point: 23°C(73°F)
• Refractive Index: 1.4115
• GHS Hazard statements: H331-H314-H318-H226
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310-P402
• Risk Statements: 5-10-14-23-35
• Safety Statements: 4-8-9-20-23-26-30-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN2920
• Packing Group: I

REFERENCES

• 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.
• 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).