Methyl isocyanide
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Names | |
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IUPAC name
Isocyanomethane
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Other names
methyl isocyanide; isoacetonitrile; methylisonitrile
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Identifiers | |
593-75-9 | |
ChEBI | CHEBI:44177 |
ChemSpider | 11156 |
DrugBank | DB04337 |
Jmol 3D model | Interactive image |
PubChem | 11646 |
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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 |
Vapor pressure | {{{value}}} |
Related compounds | |
Related compounds
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acetic acid, acetamide, ethylamine, Acetonitrile |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
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 isocyanides is very short, 1.158 Å as is characteristic of isocyanides. [1]
Preparation and uses
Methyl isocyanide was first prepared Gautier by reaction of silver cyanide with methyl iodide.[2][3] The common method for preparing methyl isocyanides is the dehydration of N-methylformamide.[4]
Methyl isocyanide is useful for the preparation of diverse heterocycles. It is also a ligand in organometallic chemistry.[5]
References
- ↑ Myer Kessler, Harold Ring, Ralph Trambarulo, Walter Gordy "Microwave Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide" Phys. Rev. 1950, vol. 79, 54–56. {{DOI:10.1103/PhysRev.79.54}}
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External links
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