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Methyl isocyanide

Methyl isocyanide
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IUPAC name
Isocyanomethane
Other names
methyl isocyanide; isoacetonitrile; methylisonitrile
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593-75-9 7pxY
ChEBI CHEBI:44177 7pxY
ChemSpider 11156 7pxY
DrugBank DB04337 7pxY
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
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C2H3N
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Appearance colorless liquid
Density 0.69 g/mL liquid
Melting point Script error: No such module "convert".
Boiling point Script error: No such module "convert".
miscible
Solubility organic solvents
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EU classification Flammable, harmful
R-phrases R11, R20/21/22, R36
S-phrases (S1/2), S16, S36/37
NFPA 704

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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