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Methyl isocyanide

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Methyl isocyanide
Names
IUPAC name
Isocyanomethane
Other names
methyl isocyanide; isoacetonitrile; methylisonitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.008.917 Edit this at Wikidata
  • InChI=1S/C2H3N/c1-3-2/h1H3 checkY
    Key: ZRKSVHFXTRFQFL-UHFFFAOYSA-N checkY
  • InChI=1/C2H3N/c1-3-2/h1H3
    Key: ZRKSVHFXTRFQFL-UHFFFAOYAI
  • [C-]#[N+]C
Properties
CH3N
Molar mass 29.042 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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
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).
checkY verify (what is checkY☒N ?)

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". Organic Syntheses. 46: 75. doi:10.15227/orgsyn.046.0075{{cite journal}}: CS1 maint: multiple names: authors list (link).
  5. ^ Eckert, H.; Nestl, A.; Ugi, I. (2001). "Methyl isocyanide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rm198.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
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