10386. Chloromethyl Chlorosulfate

Nomenclature

CAS number: 49715-04-0
Chlorosulfuric acid chloromethyl ester; chloromethoxysulfonyl chloride; CMCS.
CH2Cl2O3S; mol wt 165.00.
C 7.28%, H 1.22%, Cl 42.97%, O 29.09%, S 19.43%.

Description and references

Reagent for chloromethylation reactions. Prepn: K. Fuchs, E. Katscher, Ber. 60, 2288 (1927). Improved prepn and reactivity studies: N. P. Power et al., Org. Biomol. Chem. 2, 1554 (2004) DOI PubMed. Chloromethylation synthetic applications: E. Binderup, E. T. Hansen, Synth. Commun. 14, 857 (1984) DOI; N. Harada et al., ibid. 24, 767 (1994) DOI; A. Mntyl et al., Tetrahedron Lett. 43, 3793 (2002) DOI.

Chemical structure

Properties

Colorless liquid. Corrosive. Flammable. bp750 153-155° (dec); bp76 85-89°; bp14 49-50°. d 1.63. Flash pt: 176°F (80.0°C).

Use

Reagent in synthetic organic chemistry.