Methyl azide

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Methyl azide
Methyl azide.svg
Methyl-azide-from-MW-3D-bs-17.png
Methyl-azide-from-MW-3D-sf.png
Names
Preferred IUPAC name
Azidomethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/CH3N3/c1-3-4-2/h1H3 Yes check.svgY
    Key: PBTHJVDBCFJQGG-UHFFFAOYSA-N Yes check.svgY
  • [N-]=[N+]=N\C
Properties
CH3N3
Molar mass 57.056 g·mol−1
Appearancewhite powder
Boiling point 20–21 °C (68–70 °F; 293–294 K)
slightly soluble
Solubility alkane, ether
Explosive data
Shock sensitivity High
Friction sensitivity High
Hazards
Occupational safety and health (OHS/OSH):
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).
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Methyl azide is an organic compound with the formula CH3N3. It is a white solid and it is the simplest organic azide.

Contents

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]

Decomposition to a nitrene is a first-order reaction:

CH3N3 → CH3N + N2

The product, like its notional tautomer methanimine, polymerizes at room temperature. [3]

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
.[ citation needed ] It can be stored indefinitely in the dark at −80 °C. [1]

Related Research Articles

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In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

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.

<span class="mw-page-title-main">Nitrous acid</span> Chemical compound

Nitrous acid is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite salts. Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

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<span class="mw-page-title-main">Diethyl azodicarboxylate</span> Chemical compound

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.

<span class="mw-page-title-main">Curtius rearrangement</span> Chemical reaction

The Curtius rearrangement, first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. The isocyanate then undergoes attack by a variety of nucleophiles such as water, alcohols and amines, to yield a primary amine, carbamate or urea derivative respectively. Several reviews have been published.

<span class="mw-page-title-main">Sulfuryl chloride</span> Chemical compound

Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis.

<span class="mw-page-title-main">Sulfolene</span> Chemical compound

Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents. The compound is used as a source of butadiene.

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<span class="mw-page-title-main">Bromine azide</span> Chemical compound

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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<span class="mw-page-title-main">Togni reagent II</span> Chemical compound

Togni reagent II is a chemical compound used in organic synthesis for direct electrophilic trifluoromethylation.

An organic azide is an organic compound that contains an azide functional group. Because of the hazards associated with their use, few azides are used commercially although they exhibit interesting reactivity for researchers. Low molecular weight azides are considered especially hazardous and are avoided. In the research laboratory, azides are precursors to amines. They are also popular for their participation in the "click reaction" between an azide and an alkyne and in Staudinger ligation. These two reactions are generally quite reliable, lending themselves to combinatorial chemistry.

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.

References

  1. 1 2 Chae, Junghyun (2008-03-14), "Methyl Azide", in John Wiley & Sons, Ltd (ed.), 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
  2. Dimroth, O.; Wislicenus, W. (1905). "Ueber das Methylazid". 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.