Sulfonyl diisocyanate

Sulfonyl diisocyanate
Names
IUPAC name
Sulfuryl diisocyanate
Other names
  • Dicarbonyl-sulfamid
  • Sulfuryl bisisocyanate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.974
EC Number
  • 224-170
  • 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
Appearance Volatile 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)[1]
reacts
1.574[1]
Hazards
Flash point 113.9 °C (237.0 °F; 387.0 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

Synthesis

Sulfonyl diisocyanate is obtainable directly from certain proportions of cyanogen bromide (BrCN) and sulfur trioxide:[2]

2 BrCN + 2 SO3 → SO2(NCO)2 + Br2 + SO2

The compound can also be obtained by reacting chlorosulfonyl isocyanate (ClSO2NCO), produced by reaction of cyanogen chloride (ClCN) and SO3 with silver cyanate (AgNCO) at 150 °C (302 °F).[2]

Physical properties

Sulfonyl diisocyanate is a volatile, colorless to pale yellow liquid that reacts violently with water to form carbon dioxide (CO2) and sulfamide (SO2(NH2)2). The compound remains stable in sealed containers.[4]

Chemical properties

Sulfuryl diisocyanate reacts with dimethyl sulfoxide in acetonitrile to form sulfonyl bis (dimethylsulfilimine):[4]

SO2(NCO)2 + Me2SO → SO2[N=SMe2]2 + 2 CO2

See also

References

  1. 1 2 3 4 "Sulfuryl diisocyanate". chemsrc.com. Retrieved 14 January 2026.
  2. 1 2 3 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. 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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