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Pentafluorosulfanylbenzene

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(Redirected from Phenylsulfur pentafluoride)
Pentafluorosulfanylbenzene
Names
Preferred IUPAC name Pentafluoro(phenyl)-λ-sulfane
Other names Phenylsulfur pentafluoride, PhSF5
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.150.718 Edit this at Wikidata
EC Number
  • 621-907-3
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5F5S/c7-12(8,9,10,11)6-4-2-1-3-5-6/h1-5HKey: 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
Appearance colorless liquid
Density 1.49 g/mL
Boiling point 149 °C (300 °F; 422 K)
log P 3.36
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark GHS02: Flammable
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 , 100 kPa). Infobox references
Chemical compound

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.

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.

C 12 H 10 S 2 + 5 XeF 2 ⟶ 2 C 6 H 5 SF 5 + 5 Xe {\displaystyle {\ce {C12H10S2 + 5 XeF2 -> 2C6H5SF5 + 5Xe}}}

References

  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.
  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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