Methyl azide

Methyl azide is a covalent molecule related to hydrazoic acid and other alkyl azides.

Methyl azide

Ball-and-stick model of the methyl azide molecule Space-filling model of the methyl azide molecule
Names
Preferred IUPAC name Azidomethane
Identifiers
CAS Number	624-90-8^Y
3D model (JSmol)	Interactive image
ChemSpider	71411^Y
PubChem CID	79079
CompTox Dashboard (EPA)	DTXSID50211462
InChI InChI=1S/CH3N3/c1-3-4-2/h1H3^Y Key: PBTHJVDBCFJQGG-UHFFFAOYSA-N^Y
SMILES [N-]=[N+]=N\C
Properties
Chemical formula	CH3N3
Molar mass	57.05
Appearance	white powder
Solubility in water	slightly soluble
Solubility	alkane, ether
Explosive data
Shock sensitivity	High
Friction sensitivity	High
Hazards
Main hazards	Highly explosive
Related compounds
Related compounds	Hydrazoic acid, Chlorine azide, Ethyl azide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Preparation and properties

Methyl azide can be prepared by the methylation of sodium azide, for instance with dimethyl sulfate in alkaline solution, followed by passing through a tube of anhydrous calcium chloride or sodium hydroxide to remove contaminating hydrazoic acid.[1] The first synthesis was reported in 1905.[2]

It decomposes in a first-order reaction:[3]

CH₃N₃ → CH₃N + N₂

Methyl azide might be a potential precursor in the synthesis of prebiotic molecules via nonequilibrium reactions on interstellar ices initiated by energetic galactic cosmic rays (GCR) and photons.[4]

Safety precautions

Methyl azide is stable at ambient temperature but may explode when heated. Presence of mercury increases the sensitivity to shock and spark. It is incompatible with methanol and dimethyl malonate.[5] When heated to decomposition, it emits toxic fumes of NO_x. It can be stored indefinitely in the dark at −80 °C.[1]

References

1. Chae, Junghyun (2008-03-14), John Wiley & Sons, Ltd (ed.), "Methyl Azide", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, pp. rn00795, doi:10.1002/047084289x.rn00795, ISBN 978-0-471-93623-7, retrieved 2020-08-10
2. Dimroth, O.; Wislicenus, W. (1905). "Ueber das Methylazid" (PDF). Berichte der Deutschen Chemischen Gesellschaft. 38 (2): 1573–1576. doi:10.1002/cber.19050380254.
3. O'Dell, M. S.; Darwent, B. (1970). "Thermal decomposition of methyl azide". Canadian Journal of Chemistry. 48 (7): 1140–1147. doi:10.1139/v70-187.
4. Quinto-Hernandez, A.; Wodtke, A. M.; Bennett, C. J.; Kim, Y. S.; Kaiser, R. I. (2011). "On the Interaction of Methyl Azide (CH₃N₃) Ices with Ionizing Radiation: Formation of Methanimine (CH₂NH), Hydrogen Cyanide (HCN), and Hydrogen Isocyanide (HNC)". The Journal of Physical Chemistry A. 115 (3): 250–264. doi:10.1021/jp103028v. PMID 21162584.
5. Urben, P. G., ed. (2006). Bretherick's Handbook of Reactive Chemical Hazards (7th ed.). Elsevier. ISBN 9780123725639.

External links

• Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D. A.; Vogt, J.; Vogt, N. "CH₃N₃ Methyl azide". In Kuchitsu, K. (ed.). Group II Molecules and Radicals: Numerical Data and Functional Relationships in Science and Technology. 25 B. doi:10.1007/10653318_320.
• "Methyl azide". NIST Webbook. National Institute for Standards and Technology.

Salts and covalent derivatives of the azide ion
HN3																	He
LiN3	Be(N3)2											B(N3)3	CH3N3, C(N3)4	N(N3)3,H2N—N3	O	FN3	Ne
NaN3	Mg(N3)2											Al(N3)3	Si(N3)4	P	SO2(N3)2	ClN3	Ar
KN3	Ca(N3)2	Sc(N3)3	Ti(N3)4	VO(N3)3	Cr(N3)3, CrO2(N3)2	Mn(N3)2	Fe(N3)2, Fe(N3)3	Co(N3)2, Co(N3)3	Ni(N3)2	CuN3, Cu(N3)2	Zn(N3)2	Ga(N3)3	Ge	As	Se(N3)4	BrN3	Kr
RbN3	Sr(N3)2	Y	Zr(N3)4	Nb	Mo	Tc	Ru(N3)6^3−	Rh(N3)6^3−	Pd(N3)2	AgN3	Cd(N3)2	In	Sn	Sb	Te	IN3	Xe(N3)2
CsN3	Ba(N3)2		Hf	Ta	W	Re	Os	Ir(N3)6^3−	Pt(N3)6^2−	Au(N3)4^−	Hg2(N3)2, Hg(N3)2	TlN3	Pb(N3)2	Bi(N3)3	Po	At	Rn
Fr	Ra(N3)2		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		La	Ce(N3)3, Ce(N3)4	Pr	Nd	Pm	Sm	Eu	Gd(N3)3	Tb	Dy	Ho	Er	Tm	Yb	Lu
		Ac	Th	Pa	UO2(N3)2	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr