Tetrachlorodinitroethane

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Tetrachlorodinitroethane
1,1,2,2-Tetrachloro-1,2-dinitroethane.svg
Names
Preferred IUPAC name
1,1,2,2-Tetrachloro-1,2-dinitroethane
Other names
Tetrachlordinitroethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C2Cl4N2O4/c3-1(4,7(9)10)2(5,6)8(11)12
    Key: VDUMCAJVLOJOCK-UHFFFAOYSA-N
  • C(C([N+](=O)[O-])(Cl)Cl)([N+](=O)[O-])(Cl)Cl
Properties
C2Cl4N2O4
Molar mass 257.83 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetrachlorodinitroethane is a chlorinated nitroalkane produced by nitration of tetrachloroethylene with dinitrogen tetroxide or fuming nitric acid. [1] [2] [3] It's a powerful lachrymatory agent and pulmonary agent that is six times more toxic than chloropicrin. [3] Tetrachlorodinitroethane may be used as a fumigant. [4]

Tetrachlorodinitroethane was discovered by Hermann Kolbe in 1869 by reacting tetrachloroethylene and dinitrogen tetroxide. [5]

See also

References

  1. ↑ Argo, W. L.; James, E. M.; Donnelly, J. L. (November 1919). "Tetrachlordinitroethane". The Journal of Physical Chemistry. 23 (8): 578–585. doi:10.1021/j150197a004.
  2. ↑ Burrows, Ronald Bertram; Hunter, Louis (1932). "176. The nitration of halogenoethylenes". Journal of the Chemical Society (Resumed): 1357. doi:10.1039/JR9320001357.
  3. 1 2 Sartori, Mario (1939). The War Gases. New York: D. Van. Nostrand Co. p. 174.
  4. ↑ "Toxic agent". US3769354A.
  5. ↑ Hermann Kolbe (1869), Ueber Chlorkohlenstoffe, Berichte der Deutschen Chemischen Gesellschaft, "Berichte+der+Deutschen+Chemischen+Gesellschaft"+1869+kolbe&pg=PA629&printsec=frontcover
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