Methyl isocyanide

Methyl isocyanide
IUPAC name Isocyanomethane
Other names methyl isocyanide; isoacetonitrile; methylisonitrile
Identifiers
CAS number	593-75-9 Y
PubChem	11646
ChemSpider	11156 Y
DrugBank	DB04337
ChEBI	CHEBI:44177 Y
Jmol-3D images	Image 1
SMILES [C-]#[N+]C
InChI InChI=1S/C2H3N/c1-3-2/h1H3 Y Key: ZRKSVHFXTRFQFL-UHFFFAOYSA-N Y
Properties
Molecular formula	C2H3N
Molar mass	41.05 g mol−1
Appearance	colorless liquid
Density	0.786 g/mL liquid
Melting point	−45 °C
Boiling point	59-60 °C
Solubility in water	miscible
Solubility	organic solvents
Hazards
EU classification	Flammable, harmful
R-phrases	R11, R20/21/22, R36
S-phrases	(S1/2), S16, S36/37
NFPA 704	3 2 0
Related compounds
Related compounds	acetic acid, acetamide, ethylamine, Acetonitrile
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methyl isocyanide or Isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is structurally similar to the isomeric methyl cyanide (acetonitrile), but its reactivity is very different. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings or circlets.

Preparation

Methyl isocyanide was first prepared Gautier by reaction of silver cyanide with methyl iodide.^[1][2] The common method for preparing methyl isocyanides is the dehydration of N-methylformamide.^[3]

Uses

Methyl isocyanide is useful for the preparation of various heterocycles. It is also a ligand in organometallic chemistry.^[4]

References

1. ^ A. Gautier (1868). "Ueber eine neue Reihe von Verbindungen, welche mit den Cyanwasserstoffsäure-Aethern isomer sind". Ann. 146: 119–124. doi:10.1002/jlac.18681460107. 
2. ^ A. Gautier (1869). Ann. Chim. et Phys. 17 (103): 203. 
3. ^ Schuster, R. E.; Scott, J. E. (1973), "Methyl isocyanide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0772 
4. ^ Heiner Eckert, Alfons Nestl, Ivar Ugi, "Methyl isocyanide" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons. doi:10.1002/047084289X.rm198

External links

• WebBook page for C₂H₃N