Diethylaminosulfur trifluoride

Structural formula
General
Surname	Diethylaminosulfur trifluoride
other names	DAST; N , N -diethylaminosulfur trifluoride;
Molecular formula	C 4 H 10 SNSF 3
Brief description	yellow liquid with a pungent odor
External identifiers / databases
EC number	253-771-2
ECHA InfoCard	100,048,866
PubChem	123472
Wikidata	Q412982
properties
Molar mass	161.19 g mol −1
Physical state	liquid
density	1.22 g cm −3
boiling point	46–47 ° C (13 hPa)
solubility	Decomposes in water
safety instructions
H and P phrases	H: 226-302-312-314-332
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diethylaminosulfur trifluoride (usually referred to as DAST for short) is an organosulfur compound .

Extraction and presentation

Diethylaminosulfur trifluoride can be obtained by reacting diethylaminotrimethylsilane and sulfur tetrafluoride .

{\ displaystyle \ mathrm {Et_ {2} NSiMe_ {3} + SF_ {4} \ longrightarrow Et_ {2} NSF_ {3} + Me_ {3} SiF}}

properties

Diethylaminosulfur trifluoride is a yellow liquid with a pungent odor that decomposes in water and when heated; decomposition begins at around 50 ° C and is stormy at 90 ° C.

use

Diethylaminosulfur trifluoride is used as a mild fluorinating agent in organic chemistry. With its help, alcohols and aldehydes , for example, can be converted into the respective mono- or difluorides. It is also possible to synthesize the corresponding α-fluorothioethers from thioethers or sulfoxides . The addition of catalytic amounts of antimony trichloride or zinc chloride is sometimes advantageous.

It also serves as a catalyst in Friedel-Crafts allylations.

safety instructions

On contact with water, on heating above 90 ° C and on distillation, stormy to explosive decomposition can occur. Safe handling is only possible below 50 ° C and in solution. If the flammable liquid comes into contact with the skin or eyes, severe burns are possible.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet diethylaminosulfur trifluoride (PDF) from Merck , accessed on January 16, 2011.
↑ ^a ^b ^c data sheet (Diethylamino) sulfur trifluoride from Sigma-Aldrich , accessed on March 25, 2011 ( PDF ).
↑ WJ Middleton, EM Bingham: Diethylaminosulfur Trifluoride In: Organic Syntheses . 57, 1977, p. 50, doi : 10.15227 / orgsyn.057.0050 ; Coll. Vol. 6, 1988, p. 440 ( PDF ).
↑ ^a ^b P. G. Urben (Ed.): Bretherick's handbook of reactive chemical hazards. Volume 1 , 7th edition, Surendra-Kumar-Verlag / Elsevier, 2007, ISBN 978-0-12-373945-2 , p. 641 ( limited preview in Google book search).
↑ Organo-Fluorine Compounds, B. Baasner, H. Hagemann, JC Tatlow (eds.), Houben-Weyl / Thieme, Stuttgart, 2000.
↑ McCarthy JR, Peet NP, LeTourneau ME, Inbasekaran M., J. Am. Chem. Soc. 1985, 107, 735-737.
↑ SF Wnuk, MJ Robins, J. Org. Chem. 1990, 55, 4757-4760.
↑ MJ Robins, SF Wnuk, J. Org. Chem. 1993, 58, 3800-3801.

[Merck-1] ↑ ^a ^b ^c ^d ^e ^f data sheet diethylaminosulfur trifluoride (PDF) from Merck , accessed on January 16, 2011.

[Sigma-2] ta sheet (Diethylamino) sulfur trifluoride from Sigma-Aldrich , accessed on March 25, 2011 ( PDF ).

[3] WJ Middleton, EM Bingham: Diethylaminosulfur Trifluoride In: Organic Syntheses . 57, 1977, p. 50, doi : 10.15227 / orgsyn.057.0050 ; Coll. Vol. 6, 1988, p. 440 ( PDF ).

[Urben-4] P. G. Urben (Ed.): Bretherick's handbook of reactive chemical hazards. Volume 1 , 7th edition, Surendra-Kumar-Verlag / Elsevier, 2007, ISBN 978-0-12-373945-2 , p. 641 ( limited preview in Google book search).

[5] Organo-Fluorine Compounds, B. Baasner, H. Hagemann, JC Tatlow (eds.), Houben-Weyl / Thieme, Stuttgart, 2000.

[6] McCarthy JR, Peet NP, LeTourneau ME, Inbasekaran M., J. Am. Chem. Soc. 1985, 107, 735-737.

[7] SF Wnuk, MJ Robins, J. Org. Chem. 1990, 55, 4757-4760.

[8] MJ Robins, SF Wnuk, J. Org. Chem. 1993, 58, 3800-3801.