Bis(trifluoromethyl) disulfide (TFD) is a fluorinated organosulfur compound that was used as a
fumigant
Fumigation is a method of pest control or the removal of harmful microorganisms by completely filling an area with gaseous pesticides, or fumigants, to suffocate or poison the pests within. It is used to control pests in buildings (structural ...
. It is also an intermediate in the synthesis of
triflic acid
Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for este ...
. It is a volatile liquid that is extremely toxic by inhalation.
Synthesis
TFD can be produced by reaction of
perchloromethyl mercaptan or
thiophosgene
Thiophosgene is a red liquid with the formula . It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.
Preparation
Typically, is prepared in a two-step process ...
with
sodium fluoride
Sodium fluoride (NaF) is an inorganic compound with the formula . It is a colorless or white solid that is readily soluble in water. It is used in trace amounts in the fluoridation of drinking water to prevent tooth decay, and in toothpastes ...
.
Toxicity
TFD is extremely toxic by inhalation. TFD is a powerful
pulmonary agent
A pulmonary agent, or choking agent, is a chemical weapon agent designed to impede a victim's ability to breathe. Such compounds operate by causing a build-up of fluids in the lungs, which then leads to asphyxiation. Exposure of the eyes and sk ...
that can cause severe
pulmonary edema
Pulmonary edema (British English: oedema), also known as pulmonary congestion, is excessive fluid accumulation in the tissue or air spaces (usually alveoli) of the lungs. This leads to impaired gas exchange, most often leading to shortness ...
.
TFD is about half as toxic as
perfluoroisobutene
Perfluoroisobutene (PFIB) is the perfluorocarbon with the formula . Classified as a perfluoroalkene, it is the fluorinated counterpart of the hydrocarbon isobutene. This colorless gas is notable for its high toxicity.
Production and reactions
...
.
See also
*
Dimethyl(trifluoromethylthio)arsine
*
Perchloromethyl mercaptan
*
Thiophosgene
Thiophosgene is a red liquid with the formula . It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.
Preparation
Typically, is prepared in a two-step process ...
*
Perfluoroisobutene
Perfluoroisobutene (PFIB) is the perfluorocarbon with the formula . Classified as a perfluoroalkene, it is the fluorinated counterpart of the hydrocarbon isobutene. This colorless gas is notable for its high toxicity.
Production and reactions
...
*
Phosgene
Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of ...
References
Organic disulfides
Trifluoromethylthio compounds
Pulmonary agents
Fumigants
{{Organohalide-stub