Iron(III) azide
| Names | |
|---|---|
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| Fe(N3)3 | |
| Molar mass | 181.9053 g/mol |
| Appearance | Dark brown solid[1] |
| Melting point | Explodes |
| Solubility | Soluble in methanol |
| Hazards | |
| GHS labelling: | |
| |
| 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).
| |
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
[edit]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
[edit]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
[edit]- ^ "10". Chemical Abstracts: Volume 11. the University of Michigan: American Chemical Society. 1917. p. 2901.
- ^ a b Andrew D. White (2001). "Iron(III) Azide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289X.ri053. ISBN 0471936235.
- ^ 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.