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Cyanogen

Not to be confused with cyanamide, hydrogen cyanide, or Cyanide.
For the Android distribution, see CyanogenMod.
Cyanogen
Skeletal formula of cyanogen
Skeletal formula of cyanogen
Ball and stick model of cyanogen
Ball and stick model of cyanogen
Spacefill model of cyanogen
Spacefill model of cyanogen
Names
Preferred IUPAC name
Oxalonitrile[4]
Systematic IUPAC name
Ethanedinitrile[4]
Other names
  • Cyanogen
  • Bis(nitridocarbon)(C—C)[1]
  • Dicyan[2][3]
  • Carbon nitride[2]
  • Oxalic acid dinitrile[3]
  • Dicyanogen
  • Nitriloacetonitrile
  • CY
Identifiers
3D model (JSmol)
1732464
ChEBI
ChemSpider
ECHA InfoCard 100.006.643 Edit this at Wikidata
EC Number
  • 207-306-5
1090
MeSH cyanogen
RTECS number
  • GT1925000
UNII
UN number 1026
  • InChI=1S/C2N2/c3-1-2-4 checkY
    Key: JMANVNJQNLATNU-UHFFFAOYSA-N checkY
  • N#CC#N
Properties
N≡C−C≡N
Molar mass 52.036 g·mol−1
Appearance Colourless gas
Odor pungent, bitter almond-like
Density 950 mg/mL (at −21 °C)
Melting point −28 °C (−18 °F; 245 K)
Boiling point −21.1 °C; −6.1 °F; 252.0 K
45 g/100 mL (at 20 °C)
Solubility soluble in ethanol, ethyl ether
Vapor pressure 5.1 atm (21 °C)[5]
1.9 μmol/(Pa·kg)
−21.6·10−6 cm3/mol
1.327 (18 °C)
Thermochemistry
241.57 J/(K·mol)
309.07 kJ/mol
−1.0978–−1.0942 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 forms cyanide in the body; flammable[5]
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS09: Environmental hazard
Danger
H220, H331, H410
P210, P261, P271, P273, P304+P340, P311, P321, P377, P381, P391, P403, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
4
2
Explosive limits 6.6–32%[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[5]
REL (Recommended)
 TWA 10 ppm (20 mg/m3)[5]
IDLH (Immediate danger)
 N.D.[5]
Safety data sheet (SDS) inchem.org
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cyanogen is the chemical compound with the formula (CN)2. Its structure is N≡C−C≡N. The simplest stable carbon nitride, it is a colorless and highly toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules are linear, and consist of two CN groups ‒ analogous to diatomic halogen molecules, such as Cl2, but far less oxidizing. The two cyano groups are bonded together at their carbon atoms, though other isomers have been detected.[6] The name is also used for the CN radical,[7] and hence is used for compounds such as cyanogen bromide (Br−C≡N)[8] (but see also Cyano radical). When burned at increased pressure with oxygen, it is possible to get a blue tinted flame, the temperature of which is about 4800°C (a higher temperature is possible with ozone). It is as such regarded as the gas with the second highest temperature of burning (after dicyanoacetylene).

Cyanogen is the anhydride of oxamide:

H2N−C(=O)−C(=O)−NH2 → N≡C−C≡N + 2 H2O

though oxamide is manufactured from cyanogen by hydrolysis:[9]

N≡C−C≡N + 2 H2O → H2N−C(=O)−C(=O)−NH2
  1. ^ "oxalonitrile (CHEBI:29308)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 27 October 2006. Main. Retrieved 6 June 2012.
  2. ^ a b NIOSH Pocket Guide to Chemical Hazards. Department of Health and Human Services, Centers for Disease Control, National Institute for Occupational Safety & Health. September 2007. p. 82.
  3. ^ a b The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385. ISBN 9780911910278.
  4. ^ a b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 902. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  5. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0161". National Institute for Occupational Safety and Health (NIOSH).
  6. ^ Ringer, A. L.; Sherrill, C. D.; King, R. A.; Crawford, T. D. (2008). "Low-lying singlet excited states of isocyanogen". International Journal of Quantum Chemistry. 106 (6): 1137–1140. Bibcode:2008IJQC..108.1137R. doi:10.1002/qua.21586.
  7. ^ Irvine, William M. (2011). "Cyanogen Radical". Encyclopedia of Astrobiology. p. 402. doi:10.1007/978-3-642-11274-4_1806. ISBN 978-3-642-11271-3.
  8. ^ Hartman, W. W.; Dreger, E. E. (1931). "Cyanogen Bromide". Organic Syntheses. 11: 30; Collected Volumes, vol. 2, p. 150.
  9. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 320–321. ISBN 978-0-08-037941-8.

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