5955. Methanesulfonyl Chloride

Nomenclature

CAS number: 124-63-0
Mesyl chloride.
CH3ClO2S; mol wt 114.55.
C 10.49%, H 2.64%, Cl 30.95%, O 27.93%, S 27.99%.

Description and references

Reagent used in solution with pyridine to introduce mesyl groups in organic synthesis. Prepn: L. Carius, Ann. 114, 140 (1860); T. B. Johnson, J. M. Sprague, J. Am. Chem. Soc. 58, 1348 (1936); C. R. Noller, P. J. Hearst, ibid. 70, 3955 (1948). Environmentally-friendly synthesis: S. Mukhopadhyay et al., Chem. Commun. 2004, 472. Thermodynamics: J. P. Guthrie et al., Can. J. Chem. 76, 929 (1998). Synthetic applications: J. H. Looker, J. Org. Chem. 17, 510 (1952); W. E. Truce, C. W. Vriesen, J. Am. Chem. Soc. 75, 5032 (1953); Y. Morimoto et al., Chem. Lett. 1998, 829; P. A. Jacobi, E. H. Sessions, Jr., Synth. Commun. 33, 2575 (2003).

Chemical structure

Properties

Liquid. d418 1.4805. bp730 161°; bp21 60°. nD23 1.451. Practically insol in water; sol in alcohol, ether.

Use

In the synthesis of photographic and agricultural chemicals, pharmaceutical intermediates. As a stabilizer; catalyst; curing and chlorinating agent; precursor to methanesulfonic acid.