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38078-09-0 - Diethylaminosulfur trifluoride, 95% - DAST - A11992 - Alfa Aesar

A11992 Diethylaminosulfur trifluoride, 95%

CAS-Nummer
38078-09-0
Synonyme
DAST

Größe Preis ($) Menge Verfügbarkeit
5g 80,34
25g 257,50
100g 630,36
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Diethylaminosulfur trifluoride, 95%

MDL
MFCD00000363
EINECS
253-771-2

Chemische Eigenschaften

Formel
C4H10F3NS
Molmasse
161.19
Siedepunkt
30-32°/3mm
Flammpunkt
23°(73°F)
Dichte
1.23
Brechungsindex
1.4115
Sensitivität
Moisture Sensitive
Löslichkeit
Miscible with water, ethanol, benzene and acetonitrile.

Anwendungen

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.

Bemerkungen

Store in cool place. Moisture sensitive. It reacts with water and ethanol. Incompatible with water, acids and bases.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H331-H314-H318-H226

Toxic if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Flammable liquid and vapour.

Sicherheitshinweise: P280-P303+P361+P353-P305+P351+P338-P310-P402

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 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.

Weitere Referenzen

Beilstein
1849066
Gefahrenklasse
8
Verpackungsgruppe
I
Harmonized Tariff Code
2942.00
TSCA
No

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