Cyanogen

Cyanogen
Ball and stick model of cyanogen	Spacefill model of cyanogen
Names
	Preferred IUPAC name Oxalonitrile
	Systematic IUPAC name Ethanedinitrile
	Other names Cyanogen; Bis(nitridocarbon)(C—C); Dicyan; Carbon nitride; Oxalic acid dinitrile; Dicyanogen; Nitriloacetonitrile; CY
Identifiers
CAS Number	460-19-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1732464
ChEBI	CHEBI:29308 ;
ChemSpider	9605 ;
ECHA InfoCard	100.006.643
EC Number	207-306-5;
Gmelin Reference	1090
MeSH	cyanogen
PubChem CID	9999;
RTECS number	GT1925000;
UNII	534Q0F66RK ;
UN number	1026
CompTox Dashboard (EPA)	DTXSID1023992 ;
	InChI InChI=1S/C2N2/c3-1-2-4 Key: JMANVNJQNLATNU-UHFFFAOYSA-N ;
	SMILES N#CC#N;
Properties
Chemical formula	C2N2
Molar mass	52.036 g·mol−1
Appearance	Colourless gas
Odor	pungent, almond-like
Density	950 mg mL−1 (at −21 °C)
Melting point	−28 °C (−18 °F; 245 K)
Boiling point	−21.1 °C; −6.1 °F; 252.0 K
Solubility in water	45 g/100 mL (at 20 °C)
Solubility	soluble in ethanol, ethyl ether
Vapor pressure	5.1 atm (21 °C)
Henry's law; constant (kH)	1.9 μmol Pa−1 kg−1
Magnetic susceptibility (χ)	-21.6·10−6 cm3/mol
Refractive index (nD)	1.327 (18 °C)
Thermochemistry
Std molar; entropy (S⦵298)	241.57 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	309.07 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1.0978–−1.0942 MJ mol−1
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	forms cyanide in the body; flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220, H331, H410
Precautionary statements	P210, P261, P271, P273, P304+P340, P311, P321, P377, P381, P391, P403, P403+P233, P405, P501
NFPA 704 (fire diamond)	4 4 2
Explosive limits	6.6–32%
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (20 mg/m3)
IDLH (Immediate danger)	N.D.
Safety data sheet (SDS)	inchem.org
Related compounds
Related alkanenitriles	Hydrogen cyanide; Thiocyanic acid; Cyanogen iodide; Cyanogen bromide; Cyanogen chloride; Cyanogen fluoride; Cyanogen azide; Acetonitrile; Aminoacetonitrile; Glycolonitrile; Propionitrile; Aminopropionitrile; Malononitrile; Pivalonitrile; Acetone cyanohydrin;
Related compounds	DBNPA
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cyanogen is the chemical compound with the formula (C N)₂. The simplest stable carbon nitride, it is a colorless and highly toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules 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: N≡C‒C≡N, although 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 (NCBr)^[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 approximately 4 800 °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:

H₂NC(O)C(O)NH₂ → NCCN + 2 H₂O

although oxamide is manufactured from cyanogen by hydrolysis:^[9]

NCCN + 2 H₂O → H₂NC(O)C(O)NH₂

^ "oxalonitrile (CHEBI:29308)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 27 October 2006. Main. Retrieved 6 June 2012.
^ ^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.
^ ^a ^b The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385. ISBN 9780911910278.
^ ^a ^b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 902. doi:10.1039/9781849733069-FP001 (inactive 2024-05-09). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of May 2024 (link)
^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0161". National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ 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.
^ Hartman, W. W.; Dreger, E. E. (1931). "Cyanogen Bromide" (PDF). Organic Syntheses. 11: 30; Collected Volumes, vol. 2, p. 150.
^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 320–321. ISBN 978-0-08-037941-8.

[ChEBI-1] "oxalonitrile (CHEBI:29308)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 27 October 2006. Main. Retrieved 6 June 2012.

[Pocket-2] 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.

[Merck-3] The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385. ISBN 9780911910278.

[iupac2013-4] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 902. doi:10.1039/9781849733069-FP001 (inactive 2024-05-09). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of May 2024 (link)

[PGCH-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.

[radical-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" (PDF). Organic Syntheses. 11: 30; Collected Volumes, vol. 2, p. 150.

[greenwood-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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