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| Names | |
|---|---|
| IUPAC name Isocyanomethane | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.008.917 |
| EC Number |
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| UNII | |
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| Properties | |
| C2H3N | |
| Molar mass | 41.053 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.69 g/mL |
| Melting point | −45 °C (−49 °F; 228 K) |
| Boiling point | 59 to 60 °C (138 to 140 °F; 332 to 333 K) |
| Miscible | |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302,H312,H332,H373 | |
| P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P312,P304+P340,P312,P314,P322,P330,P363,P501 | |
| NFPA 704 (fire diamond) | |
| Related compounds | |
Related compounds | acetic acid,acetamide,ethylamine,Acetonitrile |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Methyl isocyanide orisocyanomethane is anorganic compound and a member of theisocyanide family. This colorless liquid is isomeric and isoelectronic to methyl cyanide (acetonitrile), but its reactivity is very different. In contrast to the faintly sweet, ethereal odor of acetonitrile, the smell of methyl isocyanide, like that of other simple volatile isocyanides, is distinctly penetrating and vile.[1] Methyl isocyanide is mainly used for making 5-memberedheterocyclic rings. The C-N distance in methyl isocyanide is very short, 1.158 Å as is characteristic of isocyanides.[2]
Methyl isocyanide was first prepared byA. Gautier by reaction ofsilver cyanide withmethyl iodide.[3][4] The common method for preparing methyl isocyanides is the dehydration ofN-methylformamide.[5] Many metal cyanides react with methylating agents to give complexes of methyl isocyanide.[6] This kind of reactivity has been invoked as being relevant to the origin of life.[7]
Methyl isocyanide is useful for the preparation of diverse heterocycles. It is often used to preparetransition metal isocyanide complexes.[8]
Methyl isocyanide is very endothermic (ΔfH⦵(g) = +150.2 kJ/mol, 3.66 kJ/g) and can isomerize explosively to acetonitrile.[9] A sample exploded when heated in a sealed ampoule, and during redistillation at 59 °C and 1 bar, a drop of liquid fell back into the dry boiler flask and exploded violently. The explosive decomposition of methyl isocyanide has been studied in detail.[10]
