| 词条 | Chlorosulfonyl isocyanate |
| 释义 |
| Watchedfields = changed | verifiedrevid = 450479157 | Name = Chlorosulfonyl isocyanate | ImageFile = Chlorosulfonyl-isocyanate-2D.png | ImageName = Chlorosulfonyl isocyanate | ImageFile1 = Chlorosulfonyl-isocyanate-3D-vdW.png | ImageName1 = Chlorosulfonyl isocyanate | IUPACName = Chlorosulfonyl isocyanate | OtherNames = N-Carbonylsulfamyl chloride Chloropyrosulfonyl isocyanate Sulfuryl chloride isocyanate |Section1={{Chembox Identifiers | SMILES = ClS(=O)(=O)N=C=O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 64080 | PubChem = 70918 | InChI = 1/CClNO3S/c2-7(5,6)3-1-4 | InChIKey = WRJWRGBVPUUDLA-UHFFFAOYAX | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/CClNO3S/c2-7(5,6)3-1-4 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WRJWRGBVPUUDLA-UHFFFAOYSA-N | CASNo = 1189-71-5 | CASNo_Ref = {{cascite|correct|CAS}} |Section2={{Chembox Properties | Formula = CNClO3S | MolarMass = 141.53 g/mol | Appearance = colorless liquid | Density = 1.626 g/cm3 | Solubility = decomposition | Solvent = other solvents | SolubleOther = Chlorocarbons MeCN | MeltingPtC = -44 | BoilingPtC = 107 | RefractIndex = 1.447 |Section3={{Chembox Structure | MolShape = tetrahedral at S | Dipole = |Section7={{Chembox Hazards | ExternalSDS = "External MSDS" | MainHazards = toxic, corrosive, flammable, reacts violently with water | RPhrases = {{R14}} {{R20}} {{R24/25}} {{R29}} {{R34}} {{R42/43}}[1] | SPhrases = {{S1/2}} {{S8}} {{S24}} {{S26}} {{S30}} {{S36/37/39}} {{S38}} {{S45}} [1] | NFPA-H=3|NFPA-F=1|NFPA-R=2|NFPA-S=W |Section8={{Chembox Related | OtherCompounds = Thionyl chloride Cyanogen bromide Phosphoryl chloride }} Chlorosulfonyl isocyanate is the chemical compound ClSO2NCO, known as CSI. This compound is a versatile reagent in organic synthesis. Preparation, structure, handlingCSI is prepared by treating cyanogen chloride with sulfur trioxide, the product being distilled directly from the reaction mixture.[2] 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.[3] UsesThe molecule has two electrophilic sites, the carbon and the S(VI) center.[4] 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.[5] Other reactions of CSI:
Safety considerationsCSI is toxic, corrosive and reacts violently with water. It cannot be stored in glass-stoppered flasks, requiring instead polyethylene bottles. References1. ^1 http://fscimage.fishersci.com/msds/54436.htm {{carbon compounds}}2. ^Graf, R. "Chlorosulfonyl Isocyanate" Organic Syntheses, Collected Volume 5, pages 226ff. 3. ^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. 4. ^D. N. Dhar, K. S. K. Murthy "Recent Advances in the Chemistry of Chlorosulfonyl Isocyanate" Synthesis 1986; pages 437-449. 5. ^Cremlyn, R. J. “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). {{ISBN|0-471-95512-4}} 6. ^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 4 : Inorganic carbon compounds|Reagents for organic chemistry|Isocyanates|Sulfuryl compounds |
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