Methyl isocyanide

Summary

Methyl isocyanide
Methyl isocyanide.svg
Methyl-isocyanide-3D-balls.png
Names
IUPAC name
Isocyanomethane
Other names
  • Methyl isocyanide
  • Isoacetonitrile
  • Methylisonitrile
  • Isomethanenitrile
  • Methaneisonitrile
Identifiers
  • 593-75-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:44177 checkY
ChemSpider
  • 11156 checkY
DrugBank
  • DB04337 checkY
ECHA InfoCard 100.008.917 Edit this at Wikidata
EC Number
  • 209-806-9
  • 11646
UNII
  • B5B6DXM7GG checkY
  • DTXSID3075040 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
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
GHS pictograms GHS07: Exclamation markGHS08: Health hazard
GHS Signal word Warning
H302, H312, H332, H373
P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P322, P330, P363, P501
NFPA 704 (fire diamond)
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 ?)
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. In contrast to the faintly sweet, ethereal odor of acetonitrile, the smell of methyl isocyanide, like that of other simple volatile isocyanides, is distinctly penetrating and vile. 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]

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". Methyl Isocyanide. Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rm198. ISBN 0471936235.

External links

  • "WebBook page for C2H3N".