chlorosulfonyl isocyanate
{{chembox
| Watchedfields = changed
| verifiedrevid = 450479157
| Name = Chlorosulfonyl isocyanate
| ImageFile = Chlorosulfonyl isocyanate.svg
| 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
| EINECS = 214-715-2
| 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}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2903Y990SM
}}
|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 = [http://fscimage.fishersci.com/msds/54436.htm "External MSDS"]
| MainHazards = toxic, corrosive, flammable,
reacts violently with water
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|312|314|330|332|334}}
| PPhrases = {{P-phrases|260|261|264|270|271|280|284|285|301+312|301+330+331|302+352|303+361+353|304+312|304+340|304+341|305+351+338|310|312|320|321|322|330|342+311|363|403+233|405|501}}
| 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, handling
CSI is prepared by treating cyanogen chloride with sulfur trioxide, the product being distilled directly from the reaction mixture.Graf, R. "Chlorosulfonyl Isocyanate" Organic Syntheses, Collected Volume 5, pages 226ff.
::SO3 + ClCN → ClSO2NCO
In this transformation, both the carbon and the nitrogen termini of CN are functionalized.
The structure of CSI is represented as {{chem2|Cl\sS(\dO)2\sN\dC\dO}}. It consists of two electron-withdrawing components, the chlorosulfonyl group (SO2Cl) and the isocyanate group ({{chem2|\sN\dC\dO}}). Because of its resulting electrophilicity, the use of CSI in chemical synthesis requires relatively inert solvents such as chlorocarbons, acetonitrile, and ethers.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.
Uses
The molecule has two electrophilic sites, the carbon and the S(VI) center.D. N. Dhar, K. S. K. Murthy "Recent Advances in the Chemistry of Chlorosulfonyl Isocyanate" Synthesis 1986; pages 437-449.
CSI has been employed for the preparation of β-lactams,{{Cite journal|last1=Kaur|first1=Rajneesh|last2=Singh|first2=Raman|last3=Kumar|first3=Antresh|last4=Kaur|first4=Satvinder|last5=Priyadarshi|first5=Nitesh|last6=Singhal|first6=Nitin Kumar|last7=Singh|first7=Kuldeep|date=June 2020|title=1,2,3-Triazole β-lactam conjugates as antimicrobial agents|url= |journal=Heliyon|language=en|volume=6|issue=6|pages=e04241|doi=10.1016/j.heliyon.2020.e04241|doi-access=free |pmc=7327255|pmid=32637684|bibcode=2020Heliy...604241K }} some of which are medicinally important. Thus, alkenes undergo a
Other reactions of CSI:
- Cycloaddition to alkynes to give 1,2,3-oxathiazine-2,2-dioxide-6-chlorides.
- Conversion of primary alcohols to carbamates.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
- Conversion of carboxylic acids and the acid chlorides into nitriles.
- Preparation of N,N-disubstituted sulfamides, R2NSO2NH2
- Preparation of Burgess reagent
Safety considerations
CSI is toxic, corrosive and reacts violently with water.