Cyanogen azide

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Cyanogen azide
Cyanogen azide structure.svg
Names
Preferred IUPAC name
Carbononitridic azide [1]
Other names
Cyano azide
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/CN4/c2-1-4-5-3
    Key: KWEDUNSJJZVRKR-UHFFFAOYSA-N
  • C(#N)N=[N+]=[N-]
Properties
CN4
Molar mass 68.039 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyanogen azide, N3CN or CN4, is an azide compound of carbon and nitrogen which is an oily, colourless liquid at room temperature. [2] It is a highly explosive chemical that is soluble in most organic solvents, and normally handled in dilute solution in this form. [2] [3] [4] It was first synthesised by F. D. Marsh at DuPont in the early 1960s. [2] [5] There had been earlier claims of discovering it as a crystalline solid, which were incorrect. [6]

Cyanogen azide is a primary explosive, although it is far too unstable for practical use as an explosive and is extremely dangerous outside dilute solution. [7] [8] Its use in chemistry has been as a reagent prepared in situ for use in the synthesis of chemicals such as diaminotetrazoles, either in dilute solution or as a gas at reduced pressure. [9] [10] [11] [6] [12] [13] [14] It can be synthesised at below room temperature from the reaction of sodium azide with either cyanogen chloride [2] or cyanogen bromide, [5] dissolved in a solvent such as acetonitrile; this reaction must be done with care due to the production of shock-sensitive byproducts from trace moisture. [5] [12]

Related Research Articles

<span class="mw-page-title-main">Nitrogen</span> Chemical element, symbol N and atomic number 7

Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element bond to form N2, a colorless and odorless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant uncombined element in air. Because of the volatility of nitrogen compounds, nitrogen is relatively rare in the solid parts of the Earth.

In chemistry, azide is a linear, polyatomic anion with the formula N−3 and structure −N=N+=N−. It is the conjugate base of hydrazoic acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant in air bags.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

<span class="mw-page-title-main">Sodium azide</span> Chemical compound

Sodium azide is an inorganic compound with the formula NaN3. This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is an ionic substance, is highly soluble in water, and is very acutely poisonous.

<span class="mw-page-title-main">Hydrazoic acid</span> Unstable and toxic chemical compound

Hydrazoic acid, also known as hydrogen azide or azoimide, is a compound with the chemical formula HN3. It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes.

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

A cyanogen halide is a molecule consisting of cyanide and a halogen. Cyanogen halides are chemically classified as pseudohalogens.

The Stieglitz rearrangement is a rearrangement reaction in organic chemistry which is named after the American chemist Julius Stieglitz (1867–1937) and was first investigated by him and Paul Nicholas Leech in 1913. It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines. It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift. As an example, triaryl hydroxylamines can undergo a Stieglitz rearrangement by dehydration and the shift of a phenyl group after activation with phosphorus pentachloride to yield the respective triaryl imine, a Schiff base.

Electrophilic amination is a chemical process involving the formation of a carbon–nitrogen bond through the reaction of a nucleophilic carbanion with an electrophilic source of nitrogen.

<span class="mw-page-title-main">Methyl azide</span> Chemical compound

Methyl azide is an organic compound with the formula CH3N3. It is a white solid and it is the simplest organic azide.

<span class="mw-page-title-main">Silicon tetraazide</span> Chemical compound

Silicon tetraazide is a thermally unstable binary compound of silicon and nitrogen with a nitrogen content of 85.7%. This high-energy compound combusts spontaneously and can only be studied in a solution. A further coordination to a six-fold coordinated structure such as a hexaazidosilicate ion [Si(N3)6]2− or as an adduct with bicationic ligands Si(N3)4·L2 will result in relatively stable, crystalline solids that can be handled at room temperature.

In organic chemistry, thiocarboxylic acids or carbothioic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form and a thiol form. These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common.

<span class="mw-page-title-main">4-Chlorophenyl azide</span> Chemical compound

4-Chlorophenyl azide is an organic aryl azide compound with the chemical formula C6H4ClN3. The geometry between the nitrogen atoms in the azide functional group is approximately linear while the geometry between the nitrogen and the carbon of the benzene is trigonal planar.

<span class="mw-page-title-main">Samarium(II) bromide</span> Chemical compound

Samarium(II) bromide is an inorganic compound with the chemical formula SmBr
2. It is a brown solid that is insoluble in most solvents but degrades readily in air.

<span class="mw-page-title-main">1,3-Diphenylisobenzofuran</span> Chemical compound

1,3-Diphenylisobenzofuran is a highly reactive diene that can scavenge unstable and short-lived dienophiles in a Diels-Alder reaction. It is furthermore used as a standard reagent for the determination of singlet oxygen, even in biological systems. Cycloadditions with 1,3-diphenylisobenzofuran and subsequent oxygen cleavage provide access to a variety of polyaromatics.

Azidotetrazolate (CN7−) is an anion which forms a highly explosive series of salts. The ion is made by removing a proton from 5-azido-1H-tetrazole. The molecular structure contains a five-membered ring with four nitrogen atoms, and an azido side chain connected to the carbon atom. Several salts exist, but they are unstable and spontaneously explode. Rubidium azidotetrazolate was so unstable that it explodes while crystallizing. The potassium and caesium salt also spontaneously explode when dry.

<span class="mw-page-title-main">Cyanuric bromide</span> Chemical compound

Cyanuric bromide is a heterocyclic compound with formula C3N3Br3. It contains a six-membered ring of alternating nitrogen and carbon atoms, with a bromine atom attached to each carbon. It is formed by the spontaneous trimerisation of cyanogen bromide.

<span class="mw-page-title-main">Oxalyl dicyanide</span> Chemical compound

Oxalyl dicyanide is a chemical compound with the formula C4N2O2.

<span class="mw-page-title-main">Iodine azide</span> Chemical compound

Iodine azide is an explosive inorganic compound, which in ordinary conditions is a yellow solid. Formally, it is an inter-pseudohalogen.

An organic azide is an organic compound that contains an azide functional group. Because of the hazards associated with their use, few azides are used commercially although they exhibit interesting reactivity for researchers. Low molecular weight azides are considered especially hazardous and are avoided. In the research laboratory, azides are precursors to amines. They are also popular for their participation in the "click reaction" between an azide and an alkyne and in Staudinger ligation. These two reactions are generally quite reliable, lending themselves to combinatorial chemistry.

References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 799. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 Marsh, F. D.; Hermes, M. E. (October 1964). "Cyanogen Azide". Journal of the American Chemical Society. 86 (20): 4506–4507. doi:10.1021/ja01074a071.
  3. ↑ Goldsmith, Derek (2001). "Cyanogen azide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc268. ISBN   978-0471936237.
  4. ↑ Houben-Weyl Methods of Organic Chemistry Vol. E 21e, 4th Edition Supplement: Stereoselective Synthesis: Bond Formation, C-N, C-O, C-P, C-S, C-Se, C-Si, C-Sn, C-Te. Thieme. 14 May 2014. p. 5414. ISBN   978-3-13-182284-0.
  5. 1 2 3 Marsh, F. D. (September 1972). "Cyanogen azide". The Journal of Organic Chemistry. 37 (19): 2966–2969. doi:10.1021/jo00984a012.
  6. 1 2 Lowe, Derek. "Things I Won't Work With: Cyanogen Azide". Science Translational Medicine . American Association for the Advancement of Science . Retrieved 27 April 2017.
  7. ↑ Robert Matyáš; Jiří Pachman (12 March 2013). Primary Explosives. Springer Science & Business Media. p. 111. ISBN   978-3-642-28436-6.
  8. ↑ Michael L. Madigan (13 September 2017). First Responders Handbook: An Introduction, Second Edition. CRC Press. p. 170. ISBN   978-1-351-61207-4.
  9. ↑ Gordon W. Gribble; J. Joule (3 September 2009). Progress in Heterocyclic Chemistry. Elsevier. pp. 250–1. ISBN   978-0-08-096516-1.
  10. ↑ Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 17: Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles. Thieme. 14 May 2014. p. 2082. ISBN   978-3-13-178081-2.
  11. ↑ Barry M. Trost (1991). Oxidation. Elsevier. p. 479. ISBN   978-0-08-040598-8.
  12. 1 2 Joo, Young-Hyuk; Twamley, Brendan; Garg, Sonali; Shreeve, Jean'ne M. (4 August 2008). "Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole". Angewandte Chemie International Edition. 47 (33): 6236–6239. doi:10.1002/anie.200801886. PMID   18615414.
  13. ↑ Audran, Gérard; Adiche, Chiaa; Brémond, Paul; El Abed, Douniazad; Hamadouche, Mohammed; Siri, Didier; Santelli, Maurice (March 2017). "Cycloaddition of sulfonyl azides and cyanogen azide to enamines. Quantum-chemical calculations concerning the spontaneous rearrangement of the adduct into ring-contracted amidines". Tetrahedron Letters. 58 (10): 945–948. doi:10.1016/j.tetlet.2017.01.081.
  14. ↑ Energetic Materials, Volume 1. Plenum Press. pp. 68–9. ISBN   9780306370762.
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