Cyanogen iodide

Cyanogen iodide or iodine cyanide (ICN) is a pseudohalogen composed of iodine and the cyanide group. It is a relatively volatile and highly toxic inorganic compound. It occurs as white crystals that react slowly with water to form hydrogen cyanide.[4][5][6]

Cyanogen iodide
Ball and stick model of cyanogen iodide
Spacefill model of cyanogen iodide
Names
IUPAC name
Carbononitridic iodide[1]
Systematic IUPAC name
Iodoformonitrile
Other names
Iodine cyanide[2]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.322
EC Number
  • 208-053-3
RTECS number
  • NN1750000
UNII
Properties[3]
ICN
Molar mass 152.9219 g mol−1
Appearance White crystals
Density 1.84 g mL−1
Melting point 146.7 °C (296.1 °F; 419.8 K)
Reacts
Thermochemistry
160.5–169.1 kJ mol−1
Hazards
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
3
0
Related compounds
Related alkanenitriles
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

Cyanogen iodide is prepared by combining I2 and a cyanide, most commonly sodium cyanide in ice-cold water. The product is extracted with ether.[4][5][6]

I2 + NaCN → NaI + ICN

Applications

Cyanogen iodide has been used in taxidermy as a preservative[7][8] because of its toxicity.[8]

History

Cyanogen iodide was first synthesized in 1824 by the French chemist Georges-Simon Serullas (1774–1832).[9]

Cyanogen iodide was considered one of the impurities in commercially sold iodine before the 1930s.

Hazards

Cyanogen iodide is toxic if inhaled or ingested and may be fatal if swallowed or absorbed through the skin. Cyanogen iodide may cause convulsions, paralysis and death from respiratory failure. It is a strong irritant and may cause burns to the eyes and skin if contacted. If cyanogen iodide is heated enough to undergo complete decomposition, it may releases toxic fumes of nitrogen oxides, cyanide and iodide. A fire may cause the release of poisonous gas. Cyanogen iodide decomposes when contacted with acids, bases, ammonia, alcohols, and with heating. ICN slowly reacts with water or carbon dioxide to produce hydrogen cyanide.[8][10][11][12]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[13]

Solutions in pyridine

Cyanogen iodide solutions in pyridine conduct electric current. Dilute solutions of ICN in pyridine are colorless at first, but upon standing become successively yellow, orange, red-brown and deep red-brown. This effect is due to a change in conductivity, which in turn is due to the formation of an electrolyte. When electrical conductivity of ICN is compared with that of iodine-pyridine solutions, the formation of the electrolyte in ICN proceeds much more slowly. Results confirm that cyanides are much weaker salts in pyridine than are iodides, although cyanogen iodide solutions are able to be dissolved in pyridine giving solutions with electrical conductivity that increases over time and results in maximum values.[14]

  • "IODINE CYANIDE ICSC: 0662". INCHEM.

References
  1. "Iodine cyanide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 4 June 2012.
  2. The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385.
  3. Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3.
  4. Bak, B.; Hillebert, A. (1952). "CYANOGEN IODIDE". Organic Syntheses. 32: 29.; Collective Volume, 4, p. 207
  5. Langlois, M. (1860). "CYANOGÈNE Action de l'iode sur une solution concentrée de cyanure de potassium". Comptes Rendus. 51: 29.
  6. Langlois, M. (1860). "Ueber die Einwirkung des Jods auf concentrirte Cyankaliumlösung". Annalen der Chemie und Pharmacie. 116 (3): 288. doi:10.1002/jlac.18601160303.
  7. "Cyanogen halide". Encyclopædia Britannica (online). Encyclopædia Britannica Inc. 2012. Retrieved 2012-04-12.
  8. Pohanish, R. P. (2011). "Cyanogen iodide". Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens (6th ed.). Elsevier. p. 808. ISBN 978-1-4377-7869-4.
  9. Serullas (1824). "Nouveau composé d'iode, d'azote et de charbon ou cyanure d'iode" [New compound of iodine, nitrogen, and carbon, or cyanide of iodine]. Annales de Chimie et de Physique. 2nd series (in French). 27: 184–195.
  10. "Iodine cyanide - Compound Summary (CID 10478)". PubChem. NIH.
  11. "Iodine Cyanide; International Chemical Safety Card No. 0662 (U.S. National Version)". National Institute for Occupational Safety and Health, Centers for Disease Control and Prevention. 2005. Retrieved 2012-04-12.
  12. "Cyanogen Iodide". ChemicalBook.
  13. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. Cite journal requires |journal= (help)
  14. Audrieth, L. F.; Birr, E. J. (1933). "Anomalous Electrolytes. I. The Electrical Conductivity of Solutions of Iodine and Cyanogen Iodide in Pyridine". Journal of the American Chemical Society. 55 (2): 668–673. doi:10.1021/ja01329a030.
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