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Methyl isocyanide

Names
IUPAC name Isocyanomethane
Other names Methyl isocyanide Isoacetonitrile Methylisonitrile Isomethanenitrile Methaneisonitrile
Identifiers
CAS Number	593-75-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:44177
ChemSpider	11156
DrugBank	DB04337
ECHA InfoCard	100.008.917
EC Number	209-806-9
PubChem CID	11646
UNII	B5B6DXM7GG
CompTox Dashboard (EPA)	DTXSID3075040
InChI InChI=1S/C2H3N/c1-3-2/h1H3Key: ZRKSVHFXTRFQFL-UHFFFAOYSA-N InChI=1/C2H3N/c1-3-2/h1H3Key: ZRKSVHFXTRFQFL-UHFFFAOYAI
SMILES #C
Properties
Chemical formula	C2H3N
Molar mass	41.053 g·mol
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)
Solubility in water	Miscible
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H373
Precautionary statements	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 , 100 kPa). Y verify (what is  ?) Infobox references

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.

Safety

Methyl isocyanide is very endothermic (Δ_fH(g) = +150.2 kJ/mol, 3.66 kJ/g) and can 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 decomposition of methyl isocyanide has been studied in detail.

References

1. Gergel, Max G. (March 1977). Excuse me sir, would you like to buy a kilo of isopropyl bromide?. Pierce Chemical. p. 115.
2. Kessler, Myer; Ring, Harold; Trambarulo, Ralph; Gordy, Walter (1950-07-01). "Microwave Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide". Physical Review. 79 (1). American Physical Society (APS): 54–56. Bibcode:1950PhRv...79...54K. doi:10.1103/physrev.79.54. ISSN 0031-899X.
3. 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.
4. Gautier, A. (1869). "Des Nitriles des Acides Gras: Deuxième Partie - Des Carbylamines". Annales de Chimie et de Physique. 17: 203.
5. R. E. Schuster, James E. Scott, and Joseph Casanova, Jr (1966). "Methyl isocyanide". Organic Syntheses. 46: 75. doi:10.15227/orgsyn.046.0075{{cite journal}}: CS1 maint: multiple names: authors list (link).
6. 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.
7. 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.
8. Eckert, H.; Nestl, A.; Ugi, I. (2001). "Methyl Isocyanide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rm198. ISBN 0471936235.
9. Clothier, P. Q. E.; Glionna, M. T. J.; Pritchard, H. O. (July 1985). "Thermal explosions of methyl isocyanide in spherical vessels". The Journal of Physical Chemistry. 89 (14): 2992–2996. doi:10.1021/j100260a008. ISSN 0022-3654.
10. Urben, Peter (22 May 2017). Bretherick's Handbook of Reactive Chemical Hazards | ScienceDirect. Elsevier Science. ISBN 9780081009710. Retrieved 2022-02-23.

External links

• "WebBook page for C₂H₃N".

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Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide Triatomic Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene N2H Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid Five atoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nine atoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Ten atoms or more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuterated molecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
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