Methyl isocyanide

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
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).
YesY verify (what is YesYN ?)
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. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  3. Gautier, A. (1869). "Des Nitriles des Acides Gras: Dieuxiéme Partie - Des Carbylamines". Annales de Chimie et de Physique. 17: 203.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  5. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).

External links