Chlorosulfonyl isocyanate Contents Preparation, structure, handling Uses Safety considerations References Navigation menu1189-71-5Interactive image64080100.013.37870918"External MSDS"verifye

CBr4CCl4CFCF4CI4COCO2CO3COSCSCS2CSe2C3O2C3S2SiCOxidesMetal carbonylsCarbonic acidBicarbonatesCarbonates


Inorganic carbon compoundsReagents for organic chemistryIsocyanatesSulfuryl compounds


organic synthesiscyanogen chloridesulfur trioxideisocyanatelactams
















































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.[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]



Uses


The 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:


  • Cycloaddition to alkynes to give 1,2,3-oxathiazine-2,2-dioxide-6-chlorides.

  • Conversion of primary alcohols to carbamates.[6]

  • 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. It cannot be stored in glass-stoppered flasks, requiring instead polyethylene bottles.



References



  1. ^ ab http://fscimage.fishersci.com/msds/54436.htm


  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). .mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
    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


Chlorosulfonyl isocyanate

Chlorosulfonyl isocyanate

Chlorosulfonyl isocyanate
Names

IUPAC name
Chlorosulfonyl isocyanate

Other names

N-Carbonylsulfamyl chloride
Chloropyrosulfonyl isocyanate
Sulfuryl chloride isocyanate

Identifiers

CAS Number



  • 1189-71-5 ☑Y


3D model (JSmol)


  • Interactive image


ChemSpider


  • 64080 ☑Y


ECHA InfoCard

100.013.378


PubChem CID


  • 70918





Properties

Chemical formula

CNClO3S

Molar mass
141.53 g/mol
Appearance
colorless liquid

Density
1.626 g/cm3

Melting point
 −44 °C (−47 °F; 229 K)

Boiling point
 107 °C (225 °F; 380 K)

Solubility in water

decomposition

Solubility in other solvents
Chlorocarbons
MeCN


Refractive index (nD)

1.447
Structure

Molecular shape

tetrahedral at S
Hazards
Main hazards
toxic, corrosive, flammable,
reacts violently with water

Safety data sheet

"External MSDS"

R-phrases (outdated)

R14 R20 R24/25 R29 R34 R42/43[1]

S-phrases (outdated)

(S1/2) S8 S24 S26 S30 S36/37/39 S38 S45 [1]

NFPA 704



Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gasReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g., cesium, sodiumNFPA 704 four-colored diamond

1


3


2

W



Related compounds

Related compounds


Thionyl chloride
Cyanogen bromide
Phosphoryl chloride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


☑Y verify (what is ☑Y☒N ?)

Infobox references









  • v

  • t

  • e



Compounds

  • CBr4

  • CCl4

  • CF

  • CF4

  • CI4

  • CO

  • CO2

  • CO3

  • COS

  • CS

  • CS2

  • CSe2

  • C3O2

  • C3S2

  • SiC

Carbon ions


  • Carbides [:C≡C:]2–, [::C::]4–, [:C=C=C:]4–


  • Cyanides [:C≡N:]–


  • Cyanates [:O-C≡N:]–


  • Thiocyanates [:S-C≡N:]–


  • Fulminates [:C≡N-O:]–


  • Thiofulminates [:C≡N-S:]–

Oxides and related

  • Oxides

  • Metal carbonyls

  • Carbonic acid

  • Bicarbonates

  • Carbonates







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