Methyl isocyanide

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Methyl isocyanide
Methyl isocyanide.svg
Methyl-isocyanide-3D-balls.png
Names
IUPAC name
Isocyanomethane
Other names
methyl isocyanide; isoacetonitrile; methylisonitrile
Identifiers
593-75-9 YesY
ChEBI CHEBI:44177 YesY
ChemSpider 11156 YesY
DrugBank DB04337 YesY
Jmol 3D model Interactive image
PubChem 11646
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
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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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

  1. 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}}
  2. Gautier, A. (1868). "Ueber eine neue Reihe von Verbindungen, welche mit den Cyanwasserstoffsäure-Aethern isomer sind". Justus Liebigs Annalen der Chemie. 146 (1): 119–124. doi:10.1002/jlac.18681460107. 
  3. Gautier, A. (1869). "Des Nitriles des Acides Gras: Dieuxiéme Partie - Des Carbylamines". Annales de Chimie et de Physique. 17: 203. 
  4. R. E. Schuster, James E. Scott, and Joseph Casanova, Jr (1966). "Methyl isocyanide". Org. Synth. 46: 75. doi:10.15227/orgsyn.046.0075. 
  5. Eckert, H.; Nestl, A.; Ugi, I. (2001). "Methyl isocyanide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rm198. 

External links