Methyl isocyanide

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Methyl isocyanide
Methyl isocyanide.svg
Methyl-isocyanide-3D-balls.png
Identifiers
CAS number 593-75-9 YesY
PubChem 11646
ChemSpider 11156 YesY
DrugBank DB04337
ChEBI CHEBI:44177 YesY
Jmol-3D images Image 1
Properties
Molecular formula C2H3N
Molar mass 41.05 g mol−1
Appearance colorless liquid
Density 0.786 g/mL liquid
Melting point −45 °C
Boiling point 59-60 °C
Solubility in water miscible
Solubility organic solvents
Hazards
EU classification Flammable, harmful
R-phrases R11, R20/21/22, R36
S-phrases (S1/2), S16, S36/37
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related compounds acetic acid, acetamide, ethylamine, Acetonitrile
Except where noted otherwise, 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[edit]

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[edit]

  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. ^ Schuster, R. E.; Scott, J. E. (1966), "Methyl isocyanide", Org. Synth. 46: 75 ; Coll. Vol. 5: 772 
  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[edit]