Methyl isocyanide
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| Names | |
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IUPAC name
Isocyanomethane
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| Other names
methyl isocyanide; isoacetonitrile; methylisonitrile; isomethanenitrile; methaneisonitrile
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| Identifiers | |
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3D model (Jmol)
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| DrugBank | |
| ECHA InfoCard | 100.008.917 |
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PubChem CID
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| Properties | |
| C2H3N | |
| Molar mass | 41.05 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.69 g/mL liquid |
| Melting point | −45 °C (−49 °F; 228 K) |
| Boiling point | 59 to 60 °C (138 to 140 °F; 332 to 333 K) |
| miscible | |
| Solubility | organic solvents |
| Hazards | |
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EU classification (DSD)
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Flammable, harmful |
| R-phrases | R11, R20/21/22, R36 |
| S-phrases | (S1/2), S16, S36/37 |
| NFPA 704 | |
| Related compounds | |
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Related compounds
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acetic acid, acetamide, ethylamine, Acetonitrile |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric to methyl cyanide (acetonitrile), but its reactivity is very different. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings. The C-N distance in methyl isocyanide is very short, 1.158 Å as is characteristic of isocyanides.
Methyl isocyanide was first prepared Gautier by reaction of silver cyanide with methyl iodide. The common method for preparing methyl isocyanides is the dehydration of N-methylformamide.
Methyl isocyanide is useful for the preparation of diverse heterocycles. It is also a ligand in organometallic chemistry.
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