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Sulfur chloride pentafluoride

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(Redirected from Sulfur bromide pentafluoride)
Sulfur chloride pentafluoride
Skeletal formula of sulfur chloride pentafluoride
Ball-and-stick model of the sulfur chloride pentafluoride molecule
Names
Other names Pentafluorochlorosulfanyl
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.014 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/ClF5S/c1-7(2,3,4,5)6Key: GSYNTTDHMKSMFY-UHFFFAOYSA-N
SMILES
  • ClS(F)(F)(F)(F)F
Properties
Chemical formula SF5Cl
Molar mass 162.510 g/mol
Appearance Colorless gas
Density 6.642 g/dm
Melting point −64 °C (−83 °F; 209 K)
Boiling point −19 °C (−2 °F; 254 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

Sulfur chloride pentafluoride is an inorganic compound with the formula SF5Cl. It exists as a colorless gas at room temperature and is highly toxic, like most inorganic compounds containing the pentafluorosulfide (–SF5) functional group. The compound adopts an octahedral geometry with C
4v symmetry. Sulfur chloride pentafluoride is the only commercially available reagent for adding the –SF5 group to organic compounds.

Reactivity

SF5Cl is highly reactive and toxic. In contrast, sulfur hexafluoride (SF6) is inert and nontoxic despite having a closely related chemical formula. This difference highlights the lability of the S–Cl bond in SF5Cl.

Under free-radical conditions, SF5Cl adds across double bonds. The following reaction occurs with propene:

CH
3CH=CH
2 + SF
5Cl → CH3CHClCH2SF5

The addition reaction is catalyzed by (CH3CH2)3B at around −30 °C. SF5Br is used similarly.

SF5Cl is also a precursor to O(SF5)2 and F2NSF5 (from tetrafluorohydrazine).

Synthesis

Sulfur chloropentafluoride can be synthesized by several routes, starting from two lower sulfur fluorides, sulfur tetrafluoride and disulfur decafluoride:

SF4 + Cl2 + CsF → SF5Cl + CsCl
ClF + SF4 → SF5Cl
S2F10 + Cl2 → 2 SF5Cl

The corresponding SF
5Br is prepared similarly from in-situ generated bromine monofluoride.

References

  1. ^ Nyman, F., Roberts, H. L., Seaton, T. "Sulfur Chloride Pentafluoride" Inorganic Syntheses, 1966, Volume 8, p. 160. doi:10.1002/9780470132395.ch42
  2. ^ Dolbier, William R.; et al. (2006). "A convenient and efficient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic compounds". Journal of Fluorine Chemistry. 127 (10): 1302–10. doi:10.1016/j.jfluchem.2006.05.003.
  3. Savoie, Paul R.; Welch, John T. (2015). "Preparation and Utility of Organic Pentafluorosulfanyl-Containing Compounds". Chemical Reviews. 115 (2): 1130–1190. doi:10.1021/cr500336u. PMID 25341449.
  4. Winter, Rolf; Terjeson, Robin J.; Gard, Gary L. (1998). "An Improved and Facile Preparation of SF5Br". Journal of Fluorine Chemistry. 89: 105–106. doi:10.1016/S0022-1139(98)00094-3.
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