Methyl isocyanide

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 isocyanide is very short, 1.158 Å as is characteristic of isocyanides. [1]

Not to be confused with Methyl isocyanate.
Methyl isocyanide
Names
IUPAC name
Isocyanomethane
Other names
  • Methyl isocyanide
  • Isoacetonitrile
  • Methylisonitrile
  • Isomethanenitrile
  • Methaneisonitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.008.917
UNII
Properties
C2H3N
Molar mass 41.053 g·mol−1
Appearance Colorless liquid
Density 0.69 g/mL
Melting point −45 °C (−49 °F; 228 K)
Boiling point 59 to 60 °C (138 to 140 °F; 332 to 333 K)
Miscible
Hazards
Flammable, harmful
R-phrases (outdated) R11, R20/21/22, R36
S-phrases (outdated) (S1/2), S16, S36/37
NFPA 704 (fire diamond)
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. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
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).
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Infobox references

Preparation and uses

Methyl isocyanide was first prepared by A. 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] Many metal cyanides react with methylating agents to give complexes of methyl isocyanide.[5] This kind of reactivity has been invoked as being relevant to the origin of life.[6]

Methyl isocyanide is useful for the preparation of diverse heterocycles. It is often used to prepare transition metal isocyanide complexes.[7]

References
  1. Kessler, Myer; Ring, Harold; Trambarulo, Ralph; Gordy, Walter (1950-07-01). "Microwave Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide". Physical Review. American Physical Society (APS). 79 (1): 54–56. Bibcode:1950PhRv...79...54K. doi:10.1103/physrev.79.54. ISSN 0031-899X.
  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: Deuxième 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.CS1 maint: multiple names: authors list (link)
  5. Fehlhammer, Wolf P.; Fritz, Marcus. (1993). "Emergence of a CNH and Cyano Complex Based Organometallic Chemistry". Chemical Reviews. 93 (3): 1243–1280. doi:10.1021/cr00019a016.
  6. Mariani, Angelica; Russell, David; Javelle, Thomas; Sutherland, John (2018). "A Light-Releasable Potentially Prebiotic Nucleotide Activating Agent". Journal of the American Chemical Society. 140 (28): 8657–8661. doi:10.1021/jacs.8b05189. PMC 6152610. PMID 29965757.
  7. Eckert, H.; Nestl, A.; Ugi, I. (2001). "Methyl isocyanide". Encyclopedia of Reagents for Organic Synthesis, 8 Volume Set. Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rm198. ISBN 0471936235.
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