Bis(trifluoromethyl) disulfide

Bis(trifluoromethyl) disulfide

Bis(trifluoromethyl) disulfide is a chemical compound with the formula (CF3)2S2. This colorless liquid is a reagent in organic synthesis, being used primarily in the conversion of alcohols to alkyl trifluoromethyl ethers.

Structure and Bonding

Bis(trifluoromethyl) disulfide adopts a "staggered" conformation, similar to that of ethane. The S-S bond length is 2.05 Å, which is slightly shorter than the S-S bond in elemental sulfur (2.07 Å). The C-S bond length is 1.82 Å, which is slightly longer than the C-S bond in methanethiol (1.81 Å).

Synthesis

Bis(trifluoromethyl) disulfide can be synthesized from trifluoromethanesulfonic acid and sulfur in the presence of a base such as triethylamine.

Reactions

Bis(trifluoromethyl) disulfide is primarily used in the conversion of alcohols to alkyl trifluoromethyl ethers. This reaction is typically carried out in the presence of a base such as triethylamine.

Safety

Like many organosulfur compounds, bis(trifluoromethyl) disulfide has a strong odor. It should be handled with care due to its reactivity and potential to cause irritation.

See also

• Trifluoromethanesulfonic acid
• Triethylamine
• Organosulfur compounds

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