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Bis(trifluoromethyl) disulfide

Names
Other names Hexafluorodimethyl disulfide TFD
Identifiers
CAS Number	372-64-5
3D model (JSmol)	Interactive image
ChemSpider	61112
PubChem CID	67795
CompTox Dashboard (EPA)	DTXSID4073172
InChI InChI=1S/C2F6S2/c3-1(4,5)9-10-2(6,7)8Key: CGMFFOXAQVRUAZ-UHFFFAOYSA-N
SMILES C(F)(F)(F)SSC(F)(F)F
Properties
Chemical formula	C2F6S2
Molar mass	202.13 g·mol
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 , 100 kPa). Infobox references

Bis(trifluoromethyl) disulfide (TFD) is a fluorinated organosulfur compound that was used as a fumigant. 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.

Toxicity

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

See also

• Dimethyl(trifluoromethylthio)arsine
• Perchloromethyl mercaptan
• Thiophosgene
• Perfluoroisobutene
• Phosgene

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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