3113. Diethylaminosulfur Trifluoride

Nomenclature

CAS number: 38078-09-0
(T-4)-(N-Ethylethanaminato)trifluorosulfur; DAST.
C4H10F3NS; mol wt 161.19.
C 29.81%, H 6.25%, F 35.36%, N 8.69%, S 19.89%.

Description and references

Versatile fluorinating agent. Prepn: S. P. von Halasz, O. Glemser, Ber. 103, 594 (1970); and fluorination of aldehydes and alcohols: W. J. Middleton, J. Org. Chem. 40, 574 (1975). Thermal decompn study: P. A. Messina et al., J. Fluorine Chem. 42, 137 (1989). Brief review of chemistry: K. A. Jolliffe, Aust. J. Chem. 54, 75 (2001). Review of applications in nucleophilic fluorination reactions: M. Hudlicky, Org. React. 25, 513-637 (1988); R. P. Singh, J. M. Shreeve, Synthesis 2002, 2561-2578.

Chemical structure

Properties

Pale yellow liquid, bp10 46-47°; bp12 43-44°. nD20 1.4125. d 1.22-1.23. Reacts violently with water.

Caution

Thermally unstable. Undergoes explosion or detonation when heated to >90° (Jolliffe).

Use

Nucleophilic fluorinating reagent.