Methyl isocyanide

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.

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
EC Number
  • 209-806-9
UNII
  • InChI=1S/C2H3N/c1-3-2/h1H3 Y
    Key: ZRKSVHFXTRFQFL-UHFFFAOYSA-N Y
  • 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 labelling:
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).
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Infobox references
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