Tetraazidomethane

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Tetraazidomethane
Tetraazidomethane Tetraazidomethane.png
Tetraazidomethane
Tetraazidomethane Tetraazidomethane-3D-vdW.png
Tetraazidomethane
Names
Preferred IUPAC name
Tetraazidomethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 Yes check.svgY
    Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5
    Key: PGNZIEKVQCKOBT-UHFFFAOYAX
  • [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]
Properties
C(N3)4
Molar mass 180.095 g·mol−1
AppearanceColorless liquid
Boiling point ~165 °C (estimate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetraazidomethane, C(N3)4, is a colorless, highly explosive liquid. Its chemical structure consists of a carbon atom covalently bonded to four azide functional groups.

Contents

Synthesis

It was first prepared by Klaus Banert in 2006 by reaction of trichloroacetonitrile with sodium azide. [1]

Tetraazidomethane synthesis 01.svg

Uses

As with other polyazides, tetraazidomethane has interest as a high-energy-density material with potential uses in explosives, propellants, or fireworks. [2] Silicon tetraazide is also a known compound.

Reactions

Banert has reported that tetraazidomethane participates in a number of reactions including hydrolysis, cycloaddition reactions with alkenes and alkynes, and reaction with phosphines to form phosphazenes. [1]

Tetraazidomethane chemistry 01.svg

Related Research Articles

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Lead(II) azide Pb(N3)2 is an inorganic compound. More so than other azides, it is explosive. It is used in detonators to initiate secondary explosives. In a commercially usable form, it is a white to buff powder.

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.

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

Hydrazoic acid, also known as hydrogen azide, azic acid 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. The oxidation state of the nitrogen atoms in hydrazoic acid is fractional and is -1/3. 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.

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Bromine azide is an explosive inorganic compound with the formula BrN3. It has been described as a crystal or a red liquid at room temperature. It is extremely sensitive to small variations in temperature and pressure, with explosions occurring at Δp ≥ 0.05 Torr and also upon crystallization, thus extreme caution must be observed when working with this chemical.

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

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

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Iron(III) azide, also called ferric azide, is a chemical compound with the formula Fe(N3)3. It is an extremely explosive, impact-sensitive, hygroscopic dark brown solid. This compound is used to prepare various azidoalkanes, such as n-butyl azide, from alkenes via formation of alkylboranes and subsequent anti-Markovnikov addition of azide group.

Homoleptic azido compounds are chemical compounds in which the only anion or ligand is the azide group, -N3. The breadth of homoleptic azide compounds spans nearly the entire periodic table. With rare exceptions azido compounds are highly shock sensitive and need to be handled with the upmost caution. Binary azide compounds can take on several different structures including discrete compounds, or one- two, and three-dimensional nets, leading some to dub them as "polyazides". Reactivity studies of azide compounds are relatively limited due to how sensitive they can be. The sensitivity of these compounds tends to be correlated with the amount of ionic or covalent character the azide-element bond has, with ionic character being far more stable than covalent character. Therefore, compounds such as silver or sodium azide – which have strong ionic character – tend to possess more synthetic utility than their covalent counterparts. A few other notable exceptions include polymeric networks which possess unique magnetic properties, group 13 azides which unlike most other azides decompose to nitride compounds (important materials for semiconductors), other limited uses as synthetic reagents for the transfer of azide groups, or for research into high-energy-density matter.

References

  1. 1 2 "The Exciting Chemistry of Tetraazidomethane", Klaus Banert, Young-Hyuk Joo, Tobias Ruffer, Bernhard Walfort, and Heinrich Lang, Angew. Chem. Int. Ed. 2007, 46, 1168–1171. doi : 10.1002/anie.200603960
  2. "Tetraazidomethane: Chemistry with a Bang", Chemical & Engineering News, Dec. 18, 2006, 46.