Pentafluorosulfanylbenzene

Pentafluorosulfanylbenzene
Names
	Preferred IUPAC name Pentafluoro(phenyl)-λ6-sulfane
	Other names Phenylsulfur pentafluoride, PhSF5
Identifiers
CAS Number	2557-81-5;
3D model (JSmol)	Interactive image;
ChemSpider	8118076;
ECHA InfoCard	100.150.718
EC Number	621-907-3;
PubChem CID	9942464;
CompTox Dashboard (EPA)	DTXSID90433126 ;
	InChI InChI=1S/C6H5F5S/c7-12(8,9,10,11)6-4-2-1-3-5-6/h1-5H Key: DMNYFEWFSFTYEL-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)S(F)(F)(F)(F)F;
Properties
Chemical formula	C6H5F5S
Molar mass	204.16 g·mol−1
Appearance	colorless liquid
Density	1.49 g/mL
Boiling point	149 °C (300 °F; 422 K)
log P	3.36
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H302, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P270, P271, P280, P302 P352, P303 P361 P353, P304 P340, P305 P351 P338, P321, P330, P362 P364, P370 P378, P403 P233, P403 P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pentafluorosulfanylbenzene, or phenylsulfur pentafluoride, is an organosulfur compound with the formula C₆H₅SF₅. It is colorless liquid with high chemical stability.

Reactivity

Pentafluorosulfanylbenzene possesses high chemical stability under a wide range of conditions including oxidizing, reducing, strongly acidic and strongly basic environments. For example, it does not react with a refluxing solution of sodium hydroxide in aqueous ethanol, but it can react with concentrated sulfuric acid at elevated temperatures. The pentafluorosulfanyl group is a strong electron withdrawing group, and leads to electrophilic aromatic substitution reactions at the meta position.^[2]

Synthesis

Pentafluorosulfanylbenzene was originally synthesized by fluorination of diphenyl disulfide by AgF₂, a method that suffers from low yield. The best known method of synthesis is the fluorination of diphenyl disulfide with xenon difluoride, but it still only has a 25% yield.^[3]

${\ce {C12H10S2 5 XeF2 -> 2C6H5SF5 5Xe}}$

References

^ Sheppard, William A. (1960-09-01). "Arylsulfur Trifluorides and Pentafluorides". Journal of the American Chemical Society. 82 (17): 4751–4752. doi:10.1021/ja01502a083. ISSN 0002-7863.
^ Sheppard, William A. (1962-08-01). "Arylsulfur Pentafluorides". Journal of the American Chemical Society. 84 (16): 3064–3072. doi:10.1021/ja00875a006. ISSN 0002-7863.
^ Sergeeva, Tatiana A.; Dolbier, William R. (2004-07-01). "A New Synthesis of Pentafluorosulfanylbenzene". Organic Letters. 6 (14): 2417–2419. doi:10.1021/ol0491991. ISSN 1523-7060. PMID 15228293.

[1] Sheppard, William A. (1960-09-01). "Arylsulfur Trifluorides and Pentafluorides". Journal of the American Chemical Society. 82 (17): 4751–4752. doi:10.1021/ja01502a083. ISSN 0002-7863.

[2] Sheppard, William A. (1962-08-01). "Arylsulfur Pentafluorides". Journal of the American Chemical Society. 84 (16): 3064–3072. doi:10.1021/ja00875a006. ISSN 0002-7863.

[:0-3] Sergeeva, Tatiana A.; Dolbier, William R. (2004-07-01). "A New Synthesis of Pentafluorosulfanylbenzene". Organic Letters. 6 (14): 2417–2419. doi:10.1021/ol0491991. ISSN 1523-7060. PMID 15228293.

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