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DAST

(Diethylaminosulfur Trifluoride)


Other Names:

N,N-Diethylaminosulfur trifluoride

(Diethylamino)sulfur trifluoride

Diethyl(trifluorosulfido)amine




General Information:


Structure:



CAS Number: 38078-09-0

Molecular Weight: 161.19 g/mol

Appearance: Colorless oil

Boiling Point: 30-32 C at 3 mmHg

Density: 1.22 g/mL


Diethylaminosulfur trifluoride (DAST) is a nucleophilic fluorinating agent with wide use in organic chemistry. Deoxo-Fluor is more thermally stable alternative to DAST.




Common Uses:


Fluorinating agent for converting alcohol to fluorides



Procedure excerpt:

To a solution of the SM (1.04 g, 4.5 mmol) in DCM (20 mL) was added dropwise DAST (1.09 g, 6.8 mmol) at 0 C. The reaction mixture was stirred at RT for 90 min. The mixture . . .

[full procedure]




Fluorinating agent for converting aldehydes to geminal difluorides



Procedure excerpt:

. . . the SM (640 mg, 2.58 mmol) followed by DCM (8.6 mL). The resulting clear solution was cooled to -78 C and treated dropwise with DAST (1.022 mL, 7.73 mmol). . . .

[full procedure]




Fluorinating agent for converting ketones to geminal difluorides



Procedure excerpt:

To a solution of the SM (800 mg, 2.8 mmol) in DCM (10 mL) was added DAST (1.36 g, 8.4 mmol) at RT, and the reaction mixture was stirred at RT overnight. The mixture . . .

[full procedure]




References:


1) Patent Reference: WO2016011930, page 160, (15.7 MB)

2) Patent Reference: WO2014201173, page 377, (19.7 MB)

3) Patent Reference: WO2016011930, page 152, (15.7 MB)

4) Wikipedia: Diethylaminosulfur trifluoride (link)

5) www.sigmaaldrich.com: (Diethylamino)sulfur trifluoride (link)

6) Godhaviya, P. K.; Fluorinating Reagents: Properties, Preparation, Applications and Safety