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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