Cyanogen
IUPAC name	Ethanedinitrile
Other names	Cyanogen Carbon nitride Dicyan Dicyanogen Nitriloacetonitrile Oxalic acid dinitrile Oxalonitrile Oxalyl cyanide
Identifiers
CAS number	460-19-5
SMILES	N#CC#N
Properties
Molecular formula	C2N2
Molar mass	52.04 g mol−1
Density	0.95 g cm−3 at −21 °C
Melting point	−28 °C Image File history File links Download high-resolution version (1165x289, 5 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cyanogen User:Benjah-bmm27/Old gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	−21 °C Italic text This article is about the boiling point of liquids. ...
Hazards
NFPA 704	NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 4 4 2
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Cyanogen is the chemical compound with the formula (CN)₂. It is a colorless, 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 it far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C−C≡N, although other isomers have been detected. Certain derivatives of cyanogen are also called “cyanogen” even though they contain only one CN group. For example Cyanogen bromide is the compound with the structure NCBr.^[1] The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Look up chemical compound in Wiktionary, the free dictionary. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... For alternative meanings, see color (disambiguation). ... Gas phase particles (atoms, molecules, or ions) move around freely Gas is one of the four major states of matter, consisting of freely moving atoms or molecules without a definite shape and without a definite volume. ... Look up Pungency in Wiktionary, the free dictionary. ... Aroma redirects here. ... Pseudohalogens are binary inorganic compounds of the general form XY, where X is a cyanide, cyanate, thiocyanate etc. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... This article is about the chemical compound. ... For other uses, see Carbon (disambiguation). ... R-phrases , , , S-phrases , , , , , U.S. Permissible exposure limit (PEL) 5 mg/m3 Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Cyanogen bromide is a chemical compound with the formula CNBr. ...

Cyanogen is the anhydride of oxamide: Structure of anhydride. ... Oxamide is a white crystalline solid, which is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. ...

H₂NC(O)C(O)NH₂ → NCCN + 2 H₂O

Preparation

Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide: This article or section is in need of attention from an expert on the subject. ...

2 Hg(CN)₂ → (CN)₂ + 2 HgCN

Alternatively, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides, an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.^[2] Flash point non flammable Related Compounds Other cations Nickel(II) sulfate Zinc sulfate Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Copper(II) sulfate (sulphate in most Commonwealth nations) is the chemical compound with the formula... Copper(I) cyanide, also copper cyanide, cuprous cyanide, or cupricin (CAS number [1], EINECS number 208-883-6) is a white to cream colored or sometimes greenish powdery solid that is insoluble in water. ...

2 CuSO₄ + 4 KCN → (CN)₂ + 2 CuCN + 2 K₂SO₄

Industrially, it is made by the oxidation of hydrogen cyanide, usually using chlorine over an activated silicon dioxide catalyst or nitrogen dioxide over a copper salt. It is also formed when nitrogen (N₂) and acetylene (C₂H₂) are made to react by an electrical spark or discharge.^[3] R-phrases , , , , . S-phrases , , , , , , , , . Flash point −17. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... R-phrases R42 R43 R49 S-phrases S22 S36 S37 S45 S53 Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... It has been suggested that this article or section be merged into Catalysis. ... [1] R-phrases , S-phrases , , , , , Supplementary data page Structure and properties n, εr, etc. ... For other uses, see Copper (disambiguation). ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... Acetylene (systematic name: ethyne) is a hydrocarbon belonging to the group of alkynes. ... This article is about the chemistry of hydrogen. ...

History

Cyanogen has a long history and was probably first generated by Carl Scheele around 1782 in the course of his studies of hydrogen cyanide.^{[4] [5]}The first confirmed synthesis was reported 1802, when it was used to make what we now know as cyanogen chloride. It attained importance with the growth of the fertilizer industry in the late nineteenth century and is still an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of nitrocellulose. Carl Wilhelm Scheele Scheeles house with his pharmacy in Köping. ... R-phrases , , , , . S-phrases , , , , , , , , . Flash point −17. ... Cyanogen chloride, also known as CK, is a highly toxic blood agent first proposed for use in warfare by the French. ... Spreading manure, an organic fertilizer Fertilizers (also spelled fertilisers) are compounds given to plants to promote growth; they are usually applied either via the soil, for uptake by plant roots, or by foliar feeding, for uptake through leaves. ... Skeletal formula of nitrocellulose Ball-and-stick model of a section of nitrocellulose Nitrocellulose (also: cellulose nitrate, flash paper) is a highly flammable compound formed by nitrating cellulose through, for example, exposure to nitric acid or another powerful nitrating agent. ...

Safety

Like other inorganic cyanides, cyanogen is very toxic, as it undergoes reduction to cyanide, which binds more strongly than oxygen to the cytochrome c oxidase complex, thus interrupting the mitochondrial electron transfer chain.Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions and death, depending on exposure.^[6] This article is about the chemical compound. ... Cytochrome c oxidase The enzyme cytochrome c oxidase (PDB 2OCC, EC 1. ... Electron micrograph of a mitochondrion showing its mitochondrial matrix and membranes In cell biology, a mitochondrion (plural mitochondria) is a membrane-enclosed organelle that is found in most eukaryotic cells. ... The electron transfer chain (also called the electron transport chain, ETC, e-train, or simply electron transport), is any series of protein complexes and lipid-soluble messengers that convert the reductive potential of energized electrons into a cross-membrane proton gradient. ...

Cyanogen produces the second hottest known natural flame (after Carbon subnitride) with a temperature of over 4525°C (8180°F) when it burns in oxygen.^[7] Carbon subnitride or dicyanoacetylene (C4N2) is a compound of carbon and nitrogen. ...

See also

• Pseudohalogen

Pseudohalogens are binary inorganic compounds of the general form XY, where X is a cyanide, cyanate, thiocyanate etc. ...

References

1. ^ Hartman W. W.; Dreger, E. E. "Cyanogen Bromide" Organic Syntheses, Collected Volume 2, p.150 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0150.pdf
2. ^ T. K. Brotherton, J. W. Lynn (1959). "The Synthesis And Chemistry Of Cyanogen". Chemical Reviews 59 (5): 841 - 883. doi:10.1021/cr50029a003. 
3. ^ A. A. Breneman (1959). "Showing the Progress and Development of Processes for the the manufacture of Cyanogen and its Derivates (in: THE FIXATION OF ATMOSPHERIC NITROGEN". Journal of the American Chemical Society 11 (1): 2-28. doi:10.1021/ja02126a001. 
4. ^ H. Bauer (1980). "Die ersten organisch-chemischen Synthesen". Naturwissenschaften 67 (1): 1 -6. doi:10.1007/BF00424496. 
5. ^ J. Gay-Lussac (1815). "?". Ann. chim. et phys. 96: 175. 
6. ^ Muir, GD (ed.) 1971, Hazards in the Chemical Laboratory, The Royal Institute of Chemistry, London.
7. ^ Thomas, N. & Gaydon, A. G.; Brewer, L. (March 1952), "Cyanogen Flames and the Dissociation Energy of N2", The Journal of Chemical Physics 20 (3): 369-374, <http://scitation.aip.org/getabs/servlet/GetabsServlet?prog=normal&id=JCPSA6000020000003000369000001&idtype=cvips&gifs=yes>

Chemical Reviews (usually abbreviated as ), is a peer-reviewed scientific journal, published since 1900 by the American Chemical Society. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Joseph-Louis Gay-Lussac (December 6, 1778&#8211;May 10, 1850) was a French chemist and physicist. ...

External links

• National Pollutant Inventory - Cyanide compounds fact sheet