Carbonyl diazide
IUPAC name
Carbonyl diazide
Other names
Carbonyl azide,
Carbonic diazide,
Azido ketone
3D model (JSmol)
  • InChI=1S/CN6O/c2-6-4-1(8)5-7-3
  • C(=O)(N=[N+]=[N-])N=[N+]=[N-]
Molar mass 112.052 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Carbonyl diazide is a chemical compound with the chemical formula CO(N3)2. In terms of its structure, it can be described as two azide groups −N3 covalently attached to the carbonyl group −C(=O)− by single bonds. It can be prepared by way of the reaction between triphosgene and tetra-n-butylammonium azide, in a dimethyl or diethyl solution.[1]

The first synthesis of carbonyl diazide was reported in 1894, although there have been multiple alternative syntheses since then.[2]


  1. ^ Nolan, Alex M.; Amberger, Brent K.; Esselman, Brian J.; Thimmakondu, Venkatesan S.; Stanton, John F.; Woods, R. Claude; McMahon, Robert J. (28 September 2012). "Carbonyl Diazide, OC(N3)2: Synthesis, Purification, and IR Spectrum". Inorganic Chemistry. 51 (18): 9486–9851. doi:10.1021/ic301270b. PMID 22928580. Retrieved 31 October 2023.
  2. ^ Häring, Andreas P.; Kirsch, Stefan F. (6 November 2015). "Synthesis and Chemistry of Organic Geminal Di- and Triazides". Molecules. 20 (11): 20044–20062. doi:10.3390/molecules201119675. PMC 6331879. PMID 26561796.