Sulfonyl diisocyanate

Last updated
Sulfonyl diisocyanate
Sulfonyl diisocyanate.svg
Names
IUPAC name
Sulfuryl diisocyanate
Other names
Dicarbonyl-sulfamid, sulfuryl isocyanate, sulfonyl isocyanate, sulfuryl bisisocyanate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.974 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 224-170
PubChem CID
  • InChI=1S/C2N2O4S/c5-1-3-9(7,8)4-2-6
    Key: BUXTXUBQAKIQKS-UHFFFAOYSA-N
  • O=C=NS(=O)(=O)N=C=O
Properties
C2N2O4S
Molar mass 148.09 g·mol−1
AppearanceVolatile liquid
Density 1.66 g/cm3
Melting point −20 °C (−4 °F; 253 K)
Boiling point 264.6 °C (508.3 °F; 537.8 K)
reacts with water
Hazards
Flash point 113.9 °C (237.0 °F; 387.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sulfonyl diisocyanate is an organic chemical compound of carbon, nitrogen, oxygen, and sulphur with the molecular formula C2N2O4S. [1] [2] [3]

Contents

Synthesis

Sulfonyl diisocyanate is obtainable directly from certain proportions of cyanogen bromide and sulfur trioxide: [4]

2BrCN + 3SO2 → SO2(NCO2)2 + Br2 + SO2

The compound can also be obtained by reacting chlorosulfonyl isocyanate with silver cyanide at 150 °C. [5]

Physical properties

The compound forms a volatile, colorless to pale yellow liquid that reacts violently with water to form carbon dioxide and sulfamide. The compound remains stable in sealed containers. [6]

Chemical properties

Sulfuryl diisocyanate reacts with dimethyl sulfoxide in acetonitrile to form sulfonyl bis (dimethylsulfilimine): [6]

See also

References

  1. ↑ "Sulfuryl diisocyanate". chemsrc.com. Retrieved 14 January 2026.
  2. ↑ Kharasch, N. (22 October 2013). Organic Sulfur Compounds. Elsevier. p. 492. ISBN   978-1-4832-2485-5 . Retrieved 14 January 2026.
  3. ↑ Ulrich, Henri (2 December 2012). Cycloaddition Reactions of Heterocumulenes. Elsevier. p. 176. ISBN   978-0-323-16276-0 . Retrieved 14 January 2026.
  4. ↑ The Chemistry of Organic Sulfur Compounds. Symposium Publications Division, Pergamon Press. 1961. p. 492. Retrieved 14 January 2026.
  5. ↑ Organic sulfur compounds: Volume I. New York: Symposium Publications Division, Pergamon Press. 1961. p. 492. ISBN   978-1-4832-2485-5 . Retrieved 15 January 2026.{{cite book}}: ISBN / Date incompatibility (help)
  6. 1 2 Ulrich, Henri (2009). Cumulenes in click reactions. Hoboken, NJ: Wiley. p. 492. ISBN   978-0-470-74793-3 . Retrieved 15 January 2026.
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