Trichloromethanesulfonic acid

Trichloromethanesulfonic acid
Names
Other names
  • Trichloromethylsulfonic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CHCl3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
    Key: VYGSFTVYZHNGBU-UHFFFAOYSA-N
  • C(S(=O)(=O)O)(Cl)(Cl)Cl
Properties
CCl3O3S
Molar mass 198.42 g·mol−1
Appearance Colorless liquid
Density 2.0 g/cm3
soluble
Hazards
GHS labelling:
GHS05: Corrosive
H314
P260, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trichloromethanesulfonic acid is an organochlorine compound with the chemical formula CCl3SO3H.[1] It can also be classified as an organosulfur compound, specifically a sulfonic acid (RSO3H). The compound serves as a precursor to trichloromethanesulfonate ("trichlate", CCl3SO−3) salts.[2][3]

Structure

The molecule consists of a trichloromethyl group –CCl3 bonded to a sulfonic acid group –SO3H. The strong electron-withdrawing effect of the three chlorine atoms significantly increases the acidity compared to that of methanesulfonic acid, but chlorine is less electron-withdrawing than fluorine.[4][5]

Synthesis

The acid can be prepared by the hydrolysis of trichloromethanesulfonyl chloride or via the chlorination of methanesulfonic acid.[3] One laboratory method involves the reaction of carbon tetrachloride (CCl4) with sulfur trioxide (SO3) in the presence of mercury salts, though alternative routes using chlorosulfonic acid have also been reported.

Uses

While not as widely used as triflic acid, trichloromethanesulfonic acid serves as a strong Brønsted acid catalyst in certain organic transformations, including: esterification reactions of carboxylic acids, the Friedel–Crafts acylations, and carbohydrate synthesis.

Its lower cost—compared to that of triflic acid—makes it an attractive alternative when maximum acidity is not required. The acid also finds use in the preparation of trichloromethanesulfonate salts (trichlates).[6]

References

  1. ↑ Macintyre, Jane E. (12 October 1995). Dictionary of Inorganic Compounds, Supplement 3. CRC Press. ISBN 978-0-412-49110-8. Retrieved 8 May 2026.
  2. ↑ Mertens, Alisha; Gerven, David van; Kunert, Ilka; Wickleder, Mathias S. (13 November 2023). "Trichlates, an Unattended Class of Compounds: Characterization of Cl3CSO2Cl, and (H5O2)[Cl3CSO3]". Chemistry - A European Journal. 29 (63) e202302128. Bibcode:2023ChEuJ..29E2128M. doi:10.1002/chem.202302128. ISSN 0947-6539. PMID 37611091. Retrieved 8 May 2026.
  3. 1 2 "Trichloromethanesulfonic acid". evitachem.com. Retrieved 8 May 2026.
  4. ↑ Edwards, H. G. M.; Smith, D. N. (2 December 1991). "The preparation and vibrational spectrum of trichloromethanesulphonic acid, CCl3SO3H". Journal of Molecular Structure. 263: 11–20. doi:10.1016/0022-2860(91)80051-5. ISSN 0022-2860. Retrieved 8 May 2026.
  5. ↑ Smith, Michael; March, Jerry (2007). March's advanced organic chemistry: reactions, mechanisms, and structure (6th ed.). Hoboken, N.J: Wiley-Interscience. p. 18. ISBN 978-0-471-72091-1.
  6. ↑ Mertens, Alisha; van Gerven, David; Kunert, Ilka; Wickleder, Mathias S. (13 November 2023). "Trichlates, an Unattended Class of Compounds: Characterization of Cl3 CSO2 Cl, and (H5 O2 )[Cl3 CSO3 ]". Chemistry (Weinheim an der Bergstrasse, Germany). 29 (63) e202302128. Bibcode:2023ChEuJ..29E2128M. doi:10.1002/chem.202302128. ISSN 1521-3765. PMID 37611091.
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