Bis(trifluoromethyl) disulfide

Bis(trifluoromethyl) disulfide
Names
Other names
Hexafluorodimethyl disulfide
TFD
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2F6S2/c3-1(4,5)9-10-2(6,7)8
    Key: CGMFFOXAQVRUAZ-UHFFFAOYSA-N
  • C(F)(F)(F)SSC(F)(F)F
Properties
C2F6S2
Molar mass 202.13 g·mol−1
Appearance Liquid
Boiling point 35 °C (95 °F; 308 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bis(trifluoromethyl) disulfide (TFD) is a fluorinated organosulfur compound that was used as a fumigant.[1] It is also an intermediate in the synthesis of triflic acid. It is a volatile liquid that is extremely toxic by inhalation.

Synthesis

TFD can be produced by reaction of perchloromethyl mercaptan or thiophosgene with sodium fluoride.[2]

Toxicity

TFD is extremely toxic by inhalation. TFD is a powerful pulmonary agent that can cause severe pulmonary edema.[3] TFD is about half as toxic as perfluoroisobutene.[4]

See also

References

  1. ^ "Fumigation with bis(trifluoromethyl) disulfide".
  2. ^ "Reaction of metal fluorides with thiophosgene and perchloromethyl mercaptan".
  3. ^ Nold, J. B.; Petrali, J. P.; Wall, H. G.; Moore, D. H. (1991). "Progressive Pulmonary Pathology of Two Organofluorine Compounds in Rats".
  4. ^ Timperley, Christopher M. (2000). "Highly-toxic fluorine compounds". Fluorine Chemistry at the Millennium. pp. 499–538. doi:10.1016/B978-008043405-6/50040-2. ISBN 9780080434056.


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