Methyl isocyanide

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title: "Methyl isocyanide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["isocyanides", "ligands", "foul-smelling-chemicals", "methyl-compounds", "explosive-chemicals"] topic_path: "general/isocyanides" source: "https://en.wikipedia.org/wiki/Methyl_isocyanide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 455280169 | ImageFile1 = Methyl isocyanide.svg | ImageSize1 = 180px | ImageFile2 = Methyl-isocyanide-3D-balls.png | ImageSize2 = 150px | IUPACName = Isocyanomethane | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = | ChemSpiderID = 11156 | InChI = 1/C2H3N/c1-3-2/h1H3 | InChIKey = ZRKSVHFXTRFQFL-UHFFFAOYAI | StdInChI_Ref = | StdInChI = 1S/C2H3N/c1-3-2/h1H3 | StdInChIKey_Ref = | StdInChIKey = ZRKSVHFXTRFQFL-UHFFFAOYSA-N | CASNo = 593-75-9 | CASNo_Ref = | UNII_Ref = | UNII = B5B6DXM7GG | EC_number = 209-806-9 | PubChem = 11646 | DrugBank_Ref = | DrugBank = DB04337 | SMILES = [C-]#[N+]C | RTECS = | MeSHName = | ChEBI_Ref = | ChEBI = 44177 | KEGG_Ref = | KEGG = |Section2={{Chembox Properties | H=3 | N=1 | C=2 | Appearance = Colorless liquid | Density = 0.69 g/mL | MeltingPtC = −45 | MeltingPt_notes = | BoilingPtC = 59 to 60 | BoilingPt_notes = | Solubility = Miscible | SolubleOther = | Solvent = | pKb = |Section7={{Chembox Hazards | MainHazards = | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 0 | NFPA-S = | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = | AutoignitionPt = | ExploLimits = | PEL = |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = acetic acid, acetamide, ethylamine, Acetonitrile}} Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric and isoelectronic 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.

Preparation and uses

Methyl isocyanide was first prepared by A. Gautier by reaction of silver cyanide with methyl iodide. The common method for preparing methyl isocyanides is the dehydration of N-methylformamide. Many metal cyanides react with methylating agents to give complexes of methyl isocyanide. This kind of reactivity has been invoked as being relevant to the origin of life.

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

This compound has been found in the defensive secretions of certain marine sponges.

Safety

Methyl isocyanide is very endothermic (ΔfH⦵(g) = +150.2 kJ/mol, 3.66 kJ/g) and can thus isomerize explosively to acetonitrile. A sample exploded when heated in a sealed ampoule, and during redistillation at 59 °C and 1 bar, a drop of liquid fell back into the dry boiler flask and exploded violently. The explosive properties of methyl isocyanide have been studied in detail.

References

References

  1. Gergel, Max G.. (March 1977). "Excuse me sir, would you like to buy a kilo of isopropyl bromide?". Pierce Chemical.
  2. (July 1950). "Microwave Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide". Physical Review.
  3. Gautier, A.. (1868). "Ueber eine neue Reihe von Verbindungen, welche mit den Cyanwasserstoffsäure-Aethern isomer sind". [[Justus Liebigs Annalen der Chemie]].
  4. Gautier, A.. (1869). "Des Nitriles des Acides Gras: Deuxième Partie - Des Carbylamines". [[Annales de Chimie et de Physique]].
  5. (1966). "Methyl isocyanide".
  6. (1993). "Emergence of a CNH and Cyano Complex Based Organometallic Chemistry". Chemical Reviews.
  7. (2018). "A Light-Releasable Potentially Prebiotic Nucleotide Activating Agent". Journal of the American Chemical Society.
  8. (2001). "Encyclopedia of Reagents for Organic Synthesis".
  9. (2002). "Does the Odor from Sponges of the Genus Ircinia Protect Them from Fish Predators?". Journal of Chemical Ecology.
  10. (July 1985). "Thermal explosions of methyl isocyanide in spherical vessels". The Journal of Physical Chemistry.
  11. (2017). "Bretherick's Handbook of Reactive Chemical Hazards".

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isocyanidesligandsfoul-smelling-chemicalsmethyl-compoundsexplosive-chemicals