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Chlorosulfonyl isocyanate IUPAC name Chlorosulfonyl isocyanate Other names N-Carbonylsulfamyl chloride Chloropyrosulfonyl isocyanate Sulfuryl chloride isocyanate Identifiers CAS number 1189-71-5 Y PubChem 70918 ChemSpider 64080 Y Jmol-3D images Image 1 SMILES ClS(=O)(=O)N=C=O InChI InChI=1S/CClNO3S/c2-7(5,6)3-1-4 Y Key: WRJWRGBVPUUDLA-UHFFFAOYSA-N Y InChI=1/CClNO3S/c2-7(5,6)3-1-4 Key: WRJWRGBVPUUDLA-UHFFFAOYAX Properties Molecular formula CNClO3S Molar mass 141.53 g/mol Appearance colorless liquid Density 1.626 g/cm3 Melting point -44 °C Boiling point 107 °C Solubility in water decomp. Solubility in other solvents Chlorocarbons MeCN Refractive index (nD) 1.447 Structure Molecular shape tetrahedral at S Hazards Main hazards toxic, corrosive hydrolyzes violently Related compounds Related compounds Thionayl chloride Cyanogen bromide Phosphoryl chloride  Y(what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Chlorosulfonyl isocyanate is the chemical compound ClSO2NCO, known as CSI. This compound is a versatile reagent in organic synthesis. Contents 1 Preparation, structure, handling 2 Uses 3 Safety considerations 4 References Preparation, structure, handling CSI is prepared by treating cyanogen chloride with sulfur trioxide, the product being distilled directly from the reaction mixture.[1] SO3 + ClCN → ClSO2NCO In this transformation, both the carbon and the nitrogen termini of CN are functionalized. The structure of CSI is represented as ClS(O)2-N=C=O. It consists of two electron-withdrawing components, the chlorosulfonyl group (SO2Cl) and the isocyanate group (-N=C=O). Because of its resulting electrophilicity, the use of CSI in chemical synthesis requires relatively inert solvents such as chlorocarbons, acetonitrile, and ethers.[2] Uses The molecule has two electrophilic sites, the carbon and the S(VI) center.[3] CSI has been employed for the preparation of β-lactams, some of which are medicinally important. Thus, alkenes undergo a [2+2]-cycloaddition to give the sulfonamide. The SO2Cl group can be removed simply by hydrolysis, leaving the secondary amide.[4] Other reactions of CSI: Cycloaddition to alkynes to give 1,2,3-oxathiazine-2,2-dioxide-6-chlorides. Conversion of primary alcohols to carbamates.[5] Conversion of carboxylic acids and the acid chlorides into nitriles. Preparation of N,N-disubstituted sulfamides, R2NSO2NH2 Safety considerations CSI is toxic, corrosive and reacts violently with water. It cannot be stored in glass-stoppered flasks, requiring instead polyethylene bottles. References ^ Graf, R. "Chlorosulfonyl Isocyanate" Organic Syntheses, Collected Volume 5, pages 226ff. ^ Miller, M. J.; Ghosh, M.; Guzzo, P. R.; Vogt, P. F.; Hu, J.; Filzen, G. F.; Geyer, A. G. "Chlorosulfonyl Isocyanate" in "Encyclopedia of Reagents for Organic Synthesis" 2005 John Wiley & Sons: New York. ^ D. N. Dhar, K. S. K. Murthy "Recent Advances in the Chemistry of Chlorosulfonyl Isocyanate" Synthesis 1986; pages 437-449. ^ Cremlyn, R. J. “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4 ^ Burgess, E. M.; Penton, Jr., H. R.; Taylor, E. A.; Williams, W. M. "Conversion of Primary Alcohols to Urethanes via the Inner Salt of Triethylammonium Hydroxide: Methyl (Carboxylsulfamoyl) Triethylammonium Hydroxide Methyl n-Hexylcarbamate" Organic Syntheses, Coll. Vol. 6, p.788