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;31-3-2/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	181.908 g·mol−1
Appearance	Dark brown hygroscopic leaflets
Melting point	200 °C (392 °F; 473 K) in air, 230 °C (446 °F; 503 K) in nitrogen Explodes
Solubility in water	Soluble
Solubility in methanol	Soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Related compounds
Other anions	Iron(II) azide;
Other cations	Arsenic(III) azide; Boron triazide; Chromium(III) 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 explosive, very unstable, hygroscopic dark brown solid. This compound is a reagent in organic chemistry. It forms red solutions in water.^[1]

Preparation

This compound is prepared by the reaction of sodium azide and iron(III) sulfate in methanol:^[1]

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.^[2] 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.^[3]

References

^ ^a ^b ^c ^d Fedoroff, Basil T.; Sheffield, Oliver E.; Clift, George D.; Reese, Earl F.; Aaronson, Henry A.; Dunkle, Cyrus G.; Walter, Hans; McLean, Dan C. (1960). "A - Azides - Iron Azide". Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 1, A through Azoxy. Picatinny Arsenal, NJ: U.S. Army Research and Development Command TACOM - Ardec Warheads, Energetics and Combat Support Center. p. A543. LCCN 61-61759. AD0257189, PATR2700.
^ 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.
^ Andrew D. White (2001). "Iron(III) Azide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289X.ri053. ISBN 0471936235.

[EEVol1-1] Fedoroff, Basil T.; Sheffield, Oliver E.; Clift, George D.; Reese, Earl F.; Aaronson, Henry A.; Dunkle, Cyrus G.; Walter, Hans; McLean, Dan C. (1960). "A - Azides - Iron Azide". Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 1, A through Azoxy. Picatinny Arsenal, NJ: U.S. Army Research and Development Command TACOM - Ardec Warheads, Energetics and Combat Support Center. p. A543. LCCN 61-61759. AD0257189, PATR2700.

[2] 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.

[:)-3] Andrew D. White (2001). "Iron(III) Azide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289X.ri053. ISBN 0471936235.

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