Sulfonyl diisocyanate
| Names | |
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| IUPAC name
Sulfuryl diisocyanate
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| Other names
Dicarbonyl-sulfamid, sulfuryl isocyanate, sulfonyl isocyanate, sulfuryl bisisocyanate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.021.974 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| 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) |
| 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).
Infobox references
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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 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
- Chlorosulfonyl isocyanate
- Fluorosulfonyl isocyanate
- Fluorosulfonyl azide
- Trifluoromethanesulfonyl azide
References
- ^ "Sulfuryl diisocyanate". chemsrc.com. Retrieved 14 January 2026.
- ^ Kharasch, N. (22 October 2013). Organic Sulfur Compounds. Elsevier. p. 492. ISBN 978-1-4832-2485-5. Retrieved 14 January 2026.
- ^ Ulrich, Henri (2 December 2012). Cycloaddition Reactions of Heterocumulenes. Elsevier. p. 176. ISBN 978-0-323-16276-0. Retrieved 14 January 2026.
- ^ The Chemistry of Organic Sulfur Compounds. Symposium Publications Division, Pergamon Press. 1961. p. 492. Retrieved 14 January 2026.
- ^ 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) - ^ a b Ulrich, Henri (2009). Cumulenes in click reactions. Hoboken, NJ: Wiley. p. 492. ISBN 978-0-470-74793-3. Retrieved 15 January 2026.