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 micro-organisms 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 ( ...

. 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 is prepared in a two-step process from carbon ...

with

sodium fluoride Sodium fluoride (NaF) is an inorganic compound with the formula . It is used in trace amounts in the fluoridation of drinking water, in toothpaste, in metallurgy, and as a flux. It is a colorless or white solid that is readily soluble in water. I ...

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. They operate by causing a build-up of fluids in the lungs, which then leads to suffocation. Exposure to the eyes and skin tends to ...

that can cause severe

pulmonary edema Pulmonary edema, also known as pulmonary congestion, is excessive edema, liquid accumulation in the parenchyma, tissue and pulmonary alveolus, air spaces (usually alveoli) of the lungs. It leads to impaired gas exchange and may cause hypoxemia an ...

. TFD is about half as toxic as

perfluoroisobutene Perfluoroisobutene (PFIB) is the perfluorocarbon counterpart of the hydrocarbon isobutene and has the formula (CF3)2C=CF2. An alkene, it is a colorless gas that is notable as a highly toxic perfluoroalkene. Few simple alkenes are as toxic. Safet ...

Reference

Organic disulfides Trifluoromethylthio compounds Pulmonary agents Fumigants {{Organohalide-stub

Synthesis

Toxicity

See also

Reference