Iron(III) azide

Iron(III) azide

Names
Other names Ferric azide Iron triazide
Identifiers
CAS Number	14215-32-8
3D model (JSmol)	Interactive image
ChemSpider	57449725
PubChem CID	57348355
CompTox Dashboard (EPA)	DTXSID00721622
InChI InChI=1S/Fe.3N3/c;3*1-3-2/q+3;3*-1 Key: MKNZTJIHKCVUHC-UHFFFAOYSA-N
SMILES [N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[Fe+3]
Properties
Chemical formula	Fe(N3)3
Molar mass	181.9053 g/mol
Appearance	Dark brown solid [1]
Melting point	Explodes
Solubility	Soluble in methanol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Related compounds
Other cations	Cobalt(II) azide Nickel(II) azide Copper(II) azide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 a reagent in organic chemistry.

Preparation

This compound is prepared by the reaction of sodium azide and iron(III) sulfate in methanol: ^[2]

6 NaN₃ + Fe₂(SO₄)₃ → 2 Fe(N₃)₃ + 3 Na₂SO₄

Iron(III) azide can also be formed by pulse gamma-irradiation of a mixture of iron(II) perchlorate, sodium azide, and hydrogen peroxide. ^[3] Under these conditions, a neutral N₃ radical is formed, which oxidizes the iron(II) to iron(III); the iron(III) then promptly combines with azide ions.

Application in organic chemistry

In organic chemistry, ferric azide is a reagent in the one-pot conversion of alkenes to azidoalkanes, such as n-butyl azide. The process begins with a hydroboration: an anti-Markovnikov addition of an organoborane to an alkene, followed by oxidation. The nucleophilic azide anions then displace the resulting boroxy moiety from the alkane to give an azide. ^[2]

References

1. "10". Chemical Abstracts: Volume 11. the University of Michigan: American Chemical Society. 1917. p.  2901.
2. Andrew D. White (2001). "Iron(III) Azide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289X.ri053. ISBN   0471936235.
3. George V. Buxton; Igor Janovský (1976). "Mechanism of the oxidation of iron(II) by the azide radical". Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases. 72: 1884–1886. doi:10.1039/F19767201884.