[A11992] CAS 38078-09-0 | Diethylaminosulfur trifluoride, 95%

CAS : 38078-09-0
UN# : UN2920
MDL : MFCD00000363
Hazard Class : 8
EINECS : 253-771-2
Packing Group : I

Other name :

DAST

Chemical Properties

Formula : C4H10F3NS
Formula weight : 161.19
Boiling Point : 30-32°/3mm
Flash point : 23°(73°F)
Density : 1.23
Refractive Index : 1.4115
Sensitivity : Keep Cold. Moisture Sensitive. Store under Nitrogen.
Form : Liquid
Solubility : Miscible with water, ethanol, benzene and acetonitrile.

Literature References

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.

Notes

Store in cool place. Moisture sensitive. It reacts with water and ethanol. Incompatible with water, acids and bases.Other References:Beilstein: 1849066UN#: UN2920

Grade Specifications

Grade Specifications

Hazard Statements : H331-H314-H318-H226Toxic if inhaled.Causes severe skin burns and eye damage.Causes serious eye damage.Flammable liquid and vapour.
Precautionary Statements : P280-P303+P361+P353-P305+P351+P338-P310-P402Wear 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 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.Store in a dry place.