Chlorosulfonyl isocyanate

CSI is prepared by treating cyanogen chloride with sulfur trioxide, the product being distilled directly from the reaction mixture.

[1] In this transformation, both the carbon and the nitrogen termini of CN are functionalized.

Because of its resulting electrophilicity, the use of CSI in chemical synthesis requires relatively inert solvents such as chlorocarbons, acetonitrile, and ethers.

[2] The molecule has two electrophilic sites, the carbon and the S(VI) center.

The SO2Cl group can be removed simply by hydrolysis, leaving the secondary amide.

Chlorosulfonyl isocyanate
Chlorosulfonyl isocyanate
Chlorosulfonyl isocyanate
Chlorosulfonyl isocyanate
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid